| Game # | Date | Time | Team | Opponent | Venue | Score | Result |
| Aug 23 2019 | 7:30 PM | Penetang Jr. C Kings | Midland Centennials LL #1 | North Simcoe Sports & Recreation Centre | | |
| Aug 28 2019 | 7:30 PM | Penetang Jr. C Kings | Stayner Siskins | Penetanguishene Memorial Community Centre | | |
| Aug 29 2019 | 7:30 PM | Penetang Jr. C Kings | Midland Flyers | Penetanguishene Memorial Community Centre | | |
| Sep 07 2019 | 10:10 AM | Novice Rep - Bourgeois Nissan | Elmvale Coyotes | Elmvale Community Arena | | |
| Sep 07 2019 | 5:35 PM | Midget Rep - Maloney Air | Midland Centennials | Penetanguishene Memorial Community Centre | 6-2 | W |
| Sep 08 2019 | 2:15 PM | Atom Rep - Asselin Insurance | Midland Centennials | Penetanguishene Memorial Community Centre | 4-4 | T |
| Sep 08 2019 | 4:00 PM | Bantam Rep - Paul Watson Esso | Collingwood Blackhawks | Collingwood Central Park Arena | | |
| Sep 09 2019 | 6:30 PM | Atom Rep - Asselin Insurance | Midland Centennials | North Simcoe Sports & Recreation Centre | 10-0 | W |
| Sep 13 2019 | 8:00 PM | Penetang Jr. C Kings | Barrie Jr. Colts | Penetanguishene Memorial Community Centre | | |
| Sep 14 2019 | 4:45 PM | Peewee Rep - Penetang Sand & Gravel | Midland Centennials | Penetanguishene Memorial Community Centre | 1-7 | L |
| Sep 14 2019 | 5:45 PM | Bantam AE - Royal Canadian Legion | Parry Sound Shamrocks | Parry Sound - Humphrey Arena | 1-10 | L |
| Sep 14 2019 | 7:55 PM | Midget Rep - Maloney Air | Orillia Terriers | Penetanguishene Memorial Community Centre | | |
| Sep 15 2019 | 2:00 PM | Peewee Rep - Penetang Sand & Gravel | Midland Centennials | North Simcoe Sports & Recreation Centre | 2-8 | L |
| Sep 15 2019 | 3:00 PM | Novice Rep - Bourgeois Nissan | Wasaga Beach Stars | Penetanguishene Memorial Community Centre | | |
| Sep 15 2019 | 3:20 PM | Bantam Rep - Paul Watson Esso | Midland Centennials | North Simcoe Sports & Recreation Centre | 3-1 | W |
| Sep 15 2019 | 4:20 PM | Peewee AE - Precision Auto | South Muskoka Bears AE | Bracebridge Memorial Arena | 0-2 | L |
| Sep 15 2019 | 4:50 PM | Midget Rep - Maloney Air | Midland Centennials | North Simcoe Sports & Recreation Centre | | |
| Sep 20 2019 | 8:00 PM | Penetang Jr. C Kings | Midland Flyers | Penetanguishene Memorial Community Centre | | |
| Sep 21 2019 | 10:20 AM | Peewee LL - Scotiabank | Midland Centennials LL #1 | North Simcoe Sports & Recreation Centre | 7-2 | W |
| Sep 21 2019 | 6:35 PM | Bantam AE - Royal Canadian Legion | Collingwood Blackhawks AE | Penetanguishene Memorial Community Centre | 3-3 | T |
| Sep 21 2019 | 8:15 PM | Midget AE - Olympia Sports | South Muskoka Bears AE | Penetanguishene Memorial Community Centre | 0-3 | L |
| Sep 22 2019 | 4:10 PM | Peewee AE - Precision Auto | South Muskoka Bears AE | Penetanguishene Memorial Community Centre | | |
| Sep 22 2019 | 5:20 PM | Bantam Rep - Paul Watson Esso | Collingwood Blackhawks | Penetanguishene Memorial Community Centre | | |
| Sep 23 2019 | 5:20 PM | Novice Rep - Bourgeois Nissan | Midland Centennials | North Simcoe Sports & Recreation Centre | | |
| Sep 23 2019 | 5:20 PM | Novice LL - Scotiabank | Midland Centennials LL | North Simcoe Sports & Recreation Centre | | |
| Sep 24 2019 | 6:55 PM | Peewee AE - Precision Auto | Midland Centennials AE | North Simcoe Sports & Recreation Centre | 4-2 | W |
| Sep 27-Sep 29 | Atom Rep - Asselin Insurance | Oro Early Start Tournament (9099) (Oro, ON) |
| Sep 27 2019 | 8:00 PM | Penetang Jr. C Kings | Orillia Terriers | Penetanguishene Memorial Community Centre | | |
| BC-GB43 | Sep 28 2019 | 3:15 PM | Bantam AE - Royal Canadian Legion | Elmvale AE Coyotes | Penetanguishene Memorial Community Centre | 4-5 | L |
| Sep 29 2019 | 3:00 PM | Novice LL - Scotiabank | Midland Centennials LL | Penetanguishene Memorial Community Centre | | |
| Sep 29 2019 | 3:00 PM | Novice Rep - Bourgeois Nissan | Midland Centennials | Penetanguishene Memorial Community Centre | | |
| BC-GB38 | Sep 29 2019 | 5:10 PM | Bantam AE - Royal Canadian Legion | Orillia AE Terriers | Penetanguishene Memorial Community Centre | 6-5 | W |
| BA-GB58 | Sep 29 2019 | 6:30 PM | Bantam Rep - Paul Watson Esso | Huntsville Otters | Penetanguishene Memorial Community Centre | 5-4 | W |
| BC-GB05 | Oct 01 2019 | 7:30 PM | Bantam AE - Royal Canadian Legion | Collingwood AE Blackhawks | Collingwood Central Park Arena | 2-2 | T |
| BA-GB51 | Oct 04 2019 | 7:30 PM | Bantam Rep - Paul Watson Esso | Midland Centennials | Penetanguishene Memorial Community Centre | 3-1 | W |
| MA-GB52 | Oct 04 2019 | 9:00 PM | Midget Rep - Maloney Air | Midland Centennials | Penetanguishene Memorial Community Centre | 8-3 | W |
| AE094 | Oct 05 2019 | 12:55 PM | Atom LL #1 - Pharmasave | Elmvale Coyotes 1 | Penetanguishene Memorial Community Centre | 12-0 | W |
| MPS-BT-44 | Oct 05 2019 | 1:10 PM | Bantam AE - Royal Canadian Legion | Huntsville Otters AE | CSC (Don Lough) | 3-4 | L |
| MPS-PW-26 | Oct 05 2019 | 1:40 PM | Peewee Rep - Penetang Sand & Gravel | Huntsville Otters | CSC (Jack Bionda) | 4-3 | W |
| PC-GB83 | Oct 05 2019 | 2:05 PM | Peewee AE - Precision Auto | Muskoka Rock | Penetanguishene Memorial Community Centre | 1-14 | L |
| MPS-BT-43 | Oct 05 2019 | 3:00 PM | Bantam Rep - Paul Watson Esso | Huntsville Otters | CSC (Don Lough) | 2-2 | T |
| PE66 | Oct 05 2019 | 4:25 PM | Peewee LL - Scotiabank | Elmvale Coyotes | Penetanguishene Memorial Community Centre | 13-1 | W |
| BE041 | Oct 05 2019 | 5:30 PM | Bantam LL - Hindson Marina | Midland Centennials 1 | North Simcoe SRC (MMHA) | 1-14 | L |
| MB-GB49 | Oct 05 2019 | 5:35 PM | Midget AE - Olympia Sports | Huntsville Otters AE | Penetanguishene Memorial Community Centre | 6-5 | W |
| MPS-MD-33 | Oct 05 2019 | 7:10 PM | Midget Rep - Maloney Air | Huntsville Otters | CSC (Don Lough) | 2-2 | T |
| Oct 05 2019 | 8:00 PM | Penetang Jr. C Kings | Alliston Hornets | Penetanguishene Memorial Community Centre | | |
| AA-GB40 | Oct 06 2019 | 3:00 PM | Atom Rep - Asselin Insurance | Parry Sound Shamrocks | Penetanguishene Memorial Community Centre | 8-2 | W |
| MPS-MD-76 | Oct 06 2019 | 3:00 PM | Midget AE - Olympia Sports | South Muskoka Bears AE | Bracebridge | 5-0 | W |
| AE107 | Oct 06 2019 | 4:10 PM | Atom LL #2 - Tom Smith Chev Buick GMC | Coldwater Wildcats 1 | Penetanguishene Memorial Community Centre | 4-7 | L |
| PA-GB52 | Oct 06 2019 | 5:20 PM | Peewee Rep - Penetang Sand & Gravel | Parry Sound Shamrocks | Penetanguishene Memorial Community Centre | 3-3 | T |
| BC-GB41 | Oct 06 2019 | 6:35 PM | Bantam AE - Royal Canadian Legion | Owen Sound AE Jr. Attack | Penetanguishene Memorial Community Centre | 1-5 | L |
| BE084 | Oct 06 2019 | 7:55 PM | Bantam LL - Hindson Marina | Elmvale Coyotes | Penetanguishene Memorial Community Centre | 6-4 | W |
| ME89 | Oct 06 2019 | 9:15 PM | Midget LL - Sponsor TBD | Oro Thunder 3 | Penetanguishene Memorial Community Centre | 1-4 | L |
| PE40 | Oct 07 2019 | 6:30 PM | Peewee LL - Scotiabank | Midland Centennials | North Simcoe SRC (Centennial) | 7-4 | W |
| PA-GB18 | Oct 11 2019 | 7:00 PM | Peewee Rep - Penetang Sand & Gravel | Midland Centennials | North Simcoe SRC (Centennial) | 4-5 | L |
| Oct 11 2019 | 8:00 PM | Penetang Jr. C Kings | Huntsville Otters | Penetanguishene Memorial Community Centre | | |
| MA-GB40 | Oct 11 2019 | 8:20 PM | Midget Rep - Maloney Air | Midland Centennials | North Simcoe SRC (Centennial) | 4-1 | W |
| MB-GB43 | Oct 11 2019 | 9:20 PM | Midget AE - Olympia Sports | Shelburne AE Wolves | Shelburne CDRC | 10-1 | W |
| AE102 | Oct 12 2019 | 12:55 PM | Atom LL #2 - Tom Smith Chev Buick GMC | Midland Centennials 1 | Penetanguishene Memorial Community Centre | 9-4 | W |
| AA-GB41 | Oct 12 2019 | 2:05 PM | Atom Rep - Asselin Insurance | South Muskoka Bears | Penetanguishene Memorial Community Centre | 5-3 | W |
| MPS-PW-72 | Oct 12 2019 | 2:20 PM | Peewee AE - Precision Auto | South Muskoka Bears AE | Gravenhurst | 1-6 | L |
| AE090 | Oct 12 2019 | 3:15 PM | Atom LL #1 - Pharmasave | Wasaga Beach Stars 2 | Penetanguishene Memorial Community Centre | 14-1 | W |
| MB-GB24 | Oct 12 2019 | 3:45 PM | Midget AE - Olympia Sports | Owen Sound AE Jr. Attack | JMRRC (2 - East) | 3-1 | W |
| MPS-PW-56 | Oct 12 2019 | 4:00 PM | Peewee Rep - Penetang Sand & Gravel | South Muskoka Bears | Gravenhurst | 2-4 | L |
| BC-GB39 | Oct 12 2019 | 4:25 PM | Bantam AE - Royal Canadian Legion | Wasaga Beach Stars | Penetanguishene Memorial Community Centre | 3-4 | L |
| BA-GB63 | Oct 12 2019 | 5:45 PM | Bantam Rep - Paul Watson Esso | Parry Sound Shamrocks | Penetanguishene Memorial Community Centre | 8-2 | W |
| MA-GB78 | Oct 12 2019 | 7:15 PM | Midget Rep - Maloney Air | Parry Sound Shamrocks | Penetanguishene Memorial Community Centre | 3-0 | W |
| BA-GB35 | Oct 15 2019 | 7:00 PM | Bantam Rep - Paul Watson Esso | Midland Centennials | North Simcoe SRC (Centennial) | 4-0 | W |
| Oct 18-Oct 20 | Peewee Rep - Penetang Sand & Gravel | Roy Beechey Memorial Rep Tournament Type: (9157) (Tillsonburg, ON) |
| Oct 18-Oct 20 | Bantam Rep - Paul Watson Esso | Bob Beaumont Bantam Rep Otters Classic (Huntsville, ON) |
| Oct 18 2019 | 8:00 PM | Penetang Jr. C Kings | Stayner Siskins | Penetanguishene Memorial Community Centre | | |
| MPS-MD-74 | Oct 18 2019 | 8:15 PM | Midget Rep - Maloney Air | South Muskoka Bears | Bracebridge | 1-5 | L |
| AA-GB42 | Oct 19 2019 | 12:55 PM | Atom Rep - Asselin Insurance | Huntsville Otters | Penetanguishene Memorial Community Centre | 8-1 | W |
| AE108 | Oct 19 2019 | 1:20 PM | Atom LL #2 - Tom Smith Chev Buick GMC | Wasaga Beach Stars 1 | Wasaga | 10-2 | W |
| MNH148 | Oct 19 2019 | 2:05 PM | Novice LL - Scotiabank | Midland Centennials LL | Penetanguishene Memorial Community Centre | 0-0 | T |
| BE049 | Oct 19 2019 | 4:20 PM | Bantam LL - Hindson Marina | Midland Centennials 2 | North Simcoe SRC (Centennial) | 3-7 | L |
| MB-GB34 | Oct 19 2019 | 4:25 PM | Midget AE - Olympia Sports | Shelburne AE Wolves | Penetanguishene Memorial Community Centre | 2-6 | L |
| PE80 | Oct 19 2019 | 5:00 PM | Peewee LL - Scotiabank | Wasaga Beach Stars 2 | Wasaga | 2-3 | L |
| MA-GB54 | Oct 19 2019 | 5:45 PM | Midget Rep - Maloney Air | Shelburne Wolves | Penetanguishene Memorial Community Centre | 2-4 | L |
| MNH026 | Oct 20 2019 | 1:30 PM | Novice Rep - Bourgeois Nissan | Essa Eagles | Angus Rec | 0-0 | T |
| MNH027 | Oct 20 2019 | 1:30 PM | Novice LL - Scotiabank | Essa Eagles LL | Angus Rec | 0-0 | T |
| AE088 | Oct 20 2019 | 4:10 PM | Atom LL #1 - Pharmasave | Oro Thunder | Penetanguishene Memorial Community Centre | 12-1 | W |
| MB-GB15 | Oct 20 2019 | 5:00 PM | Midget AE - Olympia Sports | Georgian Shores Lightning | Thornbury | 3-5 | L |
| PE64 | Oct 20 2019 | 5:20 PM | Peewee LL - Scotiabank | Midland Centennials | Penetanguishene Memorial Community Centre | 9-2 | W |
| BE061 | Oct 20 2019 | 5:50 PM | Bantam LL - Hindson Marina | Oro Thunder 1 | Oro | 1-13 | L |
| ME98 | Oct 20 2019 | 6:30 PM | Midget LL - Sponsor TBD | Flesherton Golden Hawks | Penetanguishene Memorial Community Centre | 2-13 | L |
| BB-GB22 | Oct 20 2019 | 7:40 PM | Bantam AE - Royal Canadian Legion | Wasaga Beach Stars | Wasaga | 0-9 | L |
| AA-GB24 | Oct 21 2019 | 6:30 PM | Atom Rep - Asselin Insurance | Midland Centennials | North Simcoe SRC (Centennial) | 6-0 | W |
| AE056 | Oct 21 2019 | 6:50 PM | Atom LL #1 - Pharmasave | Midland Centennials 1 | North Simcoe SRC (MMHA) | 7-0 | W |
| PC-GB19 | Oct 22 2019 | 7:00 PM | Peewee AE - Precision Auto | Dundalk Storm | Dundalk | 4-1 | W |
| BC-GB19 | Oct 22 2019 | 8:00 PM | Bantam AE - Royal Canadian Legion | Orillia AE Terriers | Brian Orser | 2-6 | L |
| BE023 | Oct 22 2019 | 8:10 PM | Bantam LL - Hindson Marina | Elmvale Coyotes | Elmvale | 5-6 | L |
| PA-GB06 | Oct 23 2019 | 6:40 PM | Peewee Rep - Penetang Sand & Gravel | Collingwood Blackhawks | Collingwood Central Park Arena | 7-2 | W |
| MB-GB04 | Oct 23 2019 | 8:00 PM | Midget AE - Olympia Sports | Collingwood AE Blackhawks | Collingwood (Eddie Bush) Arena | 2-2 | T |
| MA-GB27 | Oct 23 2019 | 8:15 PM | Midget Rep - Maloney Air | Flesherton Golden Hawks | Flesherton | 1-4 | L |
| BA-GB16 | Oct 24 2019 | 7:30 PM | Bantam Rep - Paul Watson Esso | Collingwood Blackhawks | Collingwood Central Park Arena | 2-2 | T |
| Oct 25-Oct 27 | Peewee AE - Precision Auto | SLMHA 2019 Atom & Pee-Wee Rep Tournament (Shallow Lake, ON) |
| Oct 25-Oct 27 | Atom Rep - Asselin Insurance | PEC Milk Tournament (8996) (Prince Edward County, ON) |
| AE109 | Oct 25 2019 | 7:20 PM | Atom LL #1 - Pharmasave | Wasaga Beach Stars 1 | Wasaga | 9-0 | W |
| Oct 25 2019 | 8:00 PM | Penetang Jr. C Kings | Caledon Golden Hawks | Penetanguishene Memorial Community Centre | | |
| Oct 26 2019 | 9:00 AM | Minor Novice - Tim Hortons | Midland Centennials LL | North Simcoe Sports & Recreation Centre | | |
| AE097 | Oct 26 2019 | 12:55 PM | Atom LL #1 - Pharmasave | Midland Centennials 2 | Penetanguishene Memorial Community Centre | 5-1 | W |
| AE105 | Oct 26 2019 | 2:05 PM | Atom LL #2 - Tom Smith Chev Buick GMC | Coldwater Wildcats 3 | Penetanguishene Memorial Community Centre | 13-0 | W |
| PA-GB53 | Oct 26 2019 | 3:15 PM | Peewee Rep - Penetang Sand & Gravel | Huntsville Otters | Penetanguishene Memorial Community Centre | 9-2 | W |
| PE70 | Oct 26 2019 | 3:40 PM | Peewee LL - Scotiabank | Wasaga Beach Stars 1 | Wasaga | 1-3 | L |
| BE085 | Oct 26 2019 | 4:30 PM | Bantam LL - Hindson Marina | Essa Eagles | Penetanguishene Memorial Community Centre | 1-10 | L |
| BC-GB49 | Oct 26 2019 | 5:50 PM | Bantam AE - Royal Canadian Legion | Huntsville Otters AE | Penetanguishene Memorial Community Centre | 4-3 | W |
| MA-GB81 | Oct 26 2019 | 7:10 PM | Midget Rep - Maloney Air | Huntsville Otters | Penetanguishene Memorial Community Centre | 4-5 | L |
| MNH039 | Oct 27 2019 | 3:00 PM | Novice LL - Scotiabank | Clearview Canucks LL | Penetanguishene Memorial Community Centre | | |
| MNH038 | Oct 27 2019 | 3:00 PM | Novice Rep - Bourgeois Nissan | Clearview Canucks | Penetanguishene Memorial Community Centre | 0-0 | T |
| AE096 | Oct 27 2019 | 4:10 PM | Atom LL #1 - Pharmasave | Coldwater Wildcats 1 | Penetanguishene Memorial Community Centre | 9-1 | W |
| AE103 | Oct 27 2019 | 5:20 PM | Atom LL #2 - Tom Smith Chev Buick GMC | Elmvale Coyotes 2 | Penetanguishene Memorial Community Centre | 13-0 | W |
| PE33 | Oct 27 2019 | 5:45 PM | Peewee LL - Scotiabank | Essa Eagles | Angus Rec | 3-2 | W |
| BE080 | Oct 27 2019 | 6:30 PM | Bantam LL - Hindson Marina | Wasaga Beach Stars 1 | Penetanguishene Memorial Community Centre | 1-9 | L |
| MB-GB31 | Oct 27 2019 | 7:50 PM | Midget AE - Olympia Sports | Collingwood AE Blackhawks | Penetanguishene Memorial Community Centre | 1-3 | L |
| BC-GB18 | Oct 27 2019 | 8:30 PM | Bantam AE - Royal Canadian Legion | Elmvale AE Coyotes | Elmvale | 4-2 | W |
| PB-GB18 | Oct 29 2019 | 6:50 PM | Peewee AE - Precision Auto | Collingwood AE3 Blackhawks | Collingwood Central Park Arena | 2-3 | L |
| BA-GB31 | Oct 29 2019 | 8:10 PM | Bantam Rep - Paul Watson Esso | Elmvale Coyotes | Elmvale | 2-7 | L |
| Nov 01-Nov 03 | Midget AE - Olympia Sports | Winston Watson Memorial Midget AE Tournament (9177) (Huntsville, ON) |
| Nov 01-Nov 03 | Midget Rep - Maloney Air | Peter Mancuso November Challenge (9026) (Niagara Falls, ON) |
| PC-GB78 | Nov 01 2019 | 7:00 PM | Peewee AE - Precision Auto | Shelburne AE Wolves | Shelburne CDRC | 2-3 | L |
| BE011 | Nov 01 2019 | 7:30 PM | Bantam LL - Hindson Marina | Coldwater Wildcats 2 | Coldwater | 2-8 | L |
| PA-GB54 | Nov 01 2019 | 7:30 PM | Peewee Rep - Penetang Sand & Gravel | South Muskoka Bears | Penetanguishene Memorial Community Centre | 5-3 | W |
| BA-GB55 | Nov 01 2019 | 8:45 PM | Bantam Rep - Paul Watson Esso | Midland Centennials | Penetanguishene Memorial Community Centre | 5-0 | W |
| MNH042 | Nov 02 2019 | 11:00 AM | Novice Rep - Bourgeois Nissan | Clearview Canucks | Stayner | 0-0 | T |
| MNH043 | Nov 02 2019 | 11:00 AM | Novice LL - Scotiabank | Clearview Canucks LL | Stayner | 0-0 | T |
| AE093 | Nov 02 2019 | 12:55 PM | Atom LL #1 - Pharmasave | Elmvale Coyotes 2 | Penetanguishene Memorial Community Centre | 8-4 | W |
| AA-GB34 | Nov 02 2019 | 2:05 PM | Atom Rep - Asselin Insurance | Collingwood Blackhawks | Penetanguishene Memorial Community Centre | 1-0 | W |
| AE118 | Nov 02 2019 | 2:30 PM | Atom LL #2 - Tom Smith Chev Buick GMC | Wasaga Beach Stars 2 | Wasaga | 16-0 | W |
| ME09 | Nov 02 2019 | 2:30 PM | Midget LL - Sponsor TBD | Coldwater Wildcats 1 | Coldwater | 0-3 | L |
| PE67 | Nov 02 2019 | 4:35 PM | Peewee LL - Scotiabank | Coldwater Wildcats 2 | Penetanguishene Memorial Community Centre | 3-5 | L |
| PC-GB70 | Nov 02 2019 | 5:45 PM | Peewee AE - Precision Auto | Shelburne AE Wolves | Penetanguishene Memorial Community Centre | 2-8 | L |
| BA-GB07 | Nov 02 2019 | 7:00 PM | Bantam Rep - Paul Watson Esso | Clearview Canucks | Creemore | 7-2 | W |
| Nov 02 2019 | 8:00 PM | Penetang Jr. C Kings | Alliston Hornets | Penetanguishene Memorial Community Centre | | |
| MNH051 | Nov 03 2019 | 10:30 AM | Novice LL - Scotiabank | Oro Thunder 1 | Oro | 0-0 | T |
| MNH050 | Nov 03 2019 | 10:30 AM | Novice Rep - Bourgeois Nissan | Oro Thunder | Oro | 0-0 | T |
| PE54 | Nov 03 2019 | 11:50 AM | Peewee LL - Scotiabank | Oro Thunder | Oro | 1-2 | L |
| AA-GB27 | Nov 03 2019 | 1:10 PM | Atom Rep - Asselin Insurance | Oro Thunder | Oro | 0-2 | L |
| AE030 | Nov 03 2019 | 2:25 PM | Atom LL #2 - Tom Smith Chev Buick GMC | Elmvale Coyotes 1 | Elmvale | 9-0 | W |
| Nov 03 2019 | 3:00 PM | Minor Novice - Tim Hortons | Midland Centennials | Penetanguishene Memorial Community Centre | | |
| AE089 | Nov 03 2019 | 4:10 PM | Atom LL #1 - Pharmasave | Wasaga Beach Stars 1 | Penetanguishene Memorial Community Centre | 14-0 | W |
| MPS-PW-41 | Nov 03 2019 | 4:30 PM | Peewee AE - Precision Auto | Muskoka Rock | Port Carling | 5-13 | L |
| PA-GB34 | Nov 03 2019 | 5:20 PM | Peewee Rep - Penetang Sand & Gravel | Shelburne Wolves | Penetanguishene Memorial Community Centre | 2-2 | T |
| MPS-BT-67 | Nov 03 2019 | 5:30 PM | Bantam Rep - Paul Watson Esso | Parry Sound Shamrocks | BOCC | 6-0 | W |
| BE081 | Nov 03 2019 | 6:35 PM | Bantam LL - Hindson Marina | Oro Thunder 2 | Penetanguishene Memorial Community Centre | 0-8 | L |
| MW17 | Nov 03 2019 | 7:00 PM | Midget LL - Sponsor TBD | Clearview Canucks 2 | Stayner | 1-1 | T |
| BC-GB42 | Nov 03 2019 | 7:55 PM | Bantam AE - Royal Canadian Legion | Collingwood AE Blackhawks | Penetanguishene Memorial Community Centre | 1-2 | L |
| Nov 08-Nov 10 | Peewee Rep - Penetang Sand & Gravel | Huntsville Peewee REP Otters Classic (9176) (Huntsville, ON) |
| Nov 08-Nov 10 | Bantam AE - Royal Canadian Legion | Georgian Shores Fall Classic (9150) (Georgian Shores, ON) |
| Nov 08-Nov 10 | Atom LL #2 - Tom Smith Chev Buick GMC | Regional Silver Stick (Collingwood, ON) |
| Nov 08-Nov 10 | Peewee LL - Scotiabank | Regional Silver Stick (Collingwood, ON) |
| AA-GB14 | Nov 08 2019 | 6:35 PM | Atom Rep - Asselin Insurance | Elmvale Coyotes | Elmvale | 4-1 | W |
| Nov 08 2019 | 8:00 PM | Penetang Jr. C Kings | Stayner Siskins | Penetanguishene Memorial Community Centre | | |
| PC-GB65 | Nov 09 2019 | 2:05 PM | Peewee AE - Precision Auto | Collingwood AE4 Blackhawks | Penetanguishene Memorial Community Centre | 5-2 | W |
| AE126 | Nov 09 2019 | 2:30 PM | Atom LL #1 - Pharmasave | Wasaga Beach Stars 2 | Wasaga | 10-1 | W |
| Nov 09 2019 | 3:00 PM | Minor Novice - Tim Hortons | Elmvale Coyotes | Elmvale Community Arena | | |
| BE082 | Nov 09 2019 | 3:15 PM | Bantam LL - Hindson Marina | Oro Thunder 1 | Penetanguishene Memorial Community Centre | 1-7 | L |
| MPS-AT-58 | Nov 09 2019 | 3:45 PM | Atom Rep - Asselin Insurance | South Muskoka Bears | Bracebridge | 5-1 | W |
| ME96 | Nov 09 2019 | 4:35 PM | Midget LL - Sponsor TBD | Oro Thunder 1 | Penetanguishene Memorial Community Centre | 0-5 | L |
| BA-GB23 | Nov 09 2019 | 6:00 PM | Bantam Rep - Paul Watson Esso | Dundalk Storm | Dundalk | 5-3 | W |
| MPS-MD-41 | Nov 09 2019 | 7:10 PM | Midget AE - Olympia Sports | Huntsville Otters AE | CSC (Don Lough) | 4-4 | T |
| MA-GB06 | Nov 09 2019 | 8:30 PM | Midget Rep - Maloney Air | Clearview Canucks | Creemore | 3-5 | L |
| MPS-AT-29 | Nov 10 2019 | 12:40 PM | Atom Rep - Asselin Insurance | Huntsville Otters | CSC (Jack Bionda) | 2-0 | W |
| MPS-BT-74 | Nov 10 2019 | 2:00 PM | Bantam Rep - Paul Watson Esso | South Muskoka Bears | Gravenhurst | 2-3 | L |
| MNH069 | Nov 10 2019 | 3:00 PM | Novice LL - Scotiabank | Coldwater Wildcats | Penetanguishene Memorial Community Centre | 0-0 | T |
| MNH068 | Nov 10 2019 | 3:00 PM | Novice Rep - Bourgeois Nissan | Dundalk Storm | Penetanguishene Memorial Community Centre | 0-0 | T |
| AE091 | Nov 10 2019 | 4:10 PM | Atom LL #1 - Pharmasave | Midland Centennials 3 | Penetanguishene Memorial Community Centre | 2-3 | L |
| BE079 | Nov 10 2019 | 5:20 PM | Bantam LL - Hindson Marina | Wasaga Beach Stars 2 | Penetanguishene Memorial Community Centre | 1-9 | L |
| MB-GB33 | Nov 10 2019 | 6:40 PM | Midget AE - Olympia Sports | Owen Sound AE Jr. Attack | Penetanguishene Memorial Community Centre | 3-1 | W |
| ME60 | Nov 10 2019 | 7:15 PM | Midget LL - Sponsor TBD | Oro Thunder 1 | Oro | 3-7 | L |
| BC-GB12 | Nov 12 2019 | 8:10 PM | Bantam AE - Royal Canadian Legion | Elmvale AE Coyotes | Elmvale | 2-1 | W |
| ME51 | Nov 14 2019 | 7:40 PM | Midget LL - Sponsor TBD | Midland Centennials 2 | North Simcoe SRC (Centennial) | 2-9 | L |
| Nov 15-Nov 17 | Atom LL #1 - Pharmasave | Orr Lake Hat Trick Tournament (Orr Lake, ON) |
| Nov 15-Nov 17 | Peewee AE - Precision Auto | Regional Silver Stick (Collingwood, ON) |
| Nov 15-Nov 17 | Bantam AE - Royal Canadian Legion | Regional Silver Stick (Collingwood, ON) |
| Nov 15 2019 | 8:00 PM | Penetang Jr. C Kings | Huntsville Otters | Penetanguishene Memorial Community Centre | | |
| PA-GB39 | Nov 15 2019 | 8:10 PM | Peewee Rep - Penetang Sand & Gravel | Shelburne Wolves | Shelburne CDRC | 4-2 | W |
| MA-GB69 | Nov 15 2019 | 8:30 PM | Midget Rep - Maloney Air | Wasaga Beach Stars | Wasaga | 5-4 | W |
| Nov 16-Nov 17 | Atom Rep - Asselin Insurance | Regional Silver Stick (Wasaga Beach, ON) |
| AE011 | Nov 16 2019 | 12:00 PM | Atom LL #2 - Tom Smith Chev Buick GMC | Coldwater Wildcats 2 | Coldwater | 6-0 | W |
| PA-GB38 | Nov 16 2019 | 2:05 PM | Peewee Rep - Penetang Sand & Gravel | Oro Thunder | Penetanguishene Memorial Community Centre | 3-6 | L |
| BA-GB50 | Nov 16 2019 | 3:20 PM | Bantam Rep - Paul Watson Esso | Oro Thunder | Penetanguishene Memorial Community Centre | 6-3 | W |
| MB-GB32 | Nov 16 2019 | 4:50 PM | Midget AE - Olympia Sports | Georgian Shores Lightning | Penetanguishene Memorial Community Centre | 2-2 | T |
| ME97 | Nov 16 2019 | 6:30 PM | Midget LL - Sponsor TBD | Oro Thunder 2 | Penetanguishene Memorial Community Centre | 2-13 | L |
| MNH083 | Nov 17 2019 | 3:00 PM | Novice LL - Scotiabank | Wasaga Beach Stars LL | Penetanguishene Memorial Community Centre | | |
| MNH082 | Nov 17 2019 | 3:00 PM | Novice Rep - Bourgeois Nissan | Wasaga Beach Stars | Penetanguishene Memorial Community Centre | | |
| AE098 | Nov 17 2019 | 4:10 PM | Atom LL #2 - Tom Smith Chev Buick GMC | Wasaga Beach Stars 2 | Penetanguishene Memorial Community Centre | 15-0 | W |
| PE60 | Nov 17 2019 | 5:20 PM | Peewee LL - Scotiabank | Wasaga Beach Stars 2 | Penetanguishene Memorial Community Centre | 1-6 | L |
| BA-GB53 | Nov 17 2019 | 6:30 PM | Bantam Rep - Paul Watson Esso | Dundalk Storm | Penetanguishene Memorial Community Centre | 4-3 | W |
| MA-GB13 | Nov 18 2019 | 7:00 PM | Midget Rep - Maloney Air | Collingwood Blackhawks | Collingwood (Eddie Bush) Arena | | |
| AA-GB37 | Nov 19 2019 | 6:30 PM | Atom Rep - Asselin Insurance | Midland Centennials | Penetanguishene Memorial Community Centre | | |
| MB-GB08 | Nov 20 2019 | 8:10 PM | Midget AE - Olympia Sports | Collingwood AE Blackhawks | Collingwood (Eddie Bush) Arena | | |
| Nov 22-Nov 24 | Midget LL - Sponsor TBD | Jake Marczenko Memorial Local League Tournament (Dorchester, ON) |
| Nov 22 2019 | 8:00 PM | Penetang Jr. C Kings | Schomberg Cougars | Penetanguishene Memorial Community Centre | | |
| MPS-MD-55 | Nov 22 2019 | 8:30 PM | Midget Rep - Maloney Air | Parry Sound Shamrocks | BOCC | | |
| MB-GB40 | Nov 22 2019 | 9:30 PM | Midget AE - Olympia Sports | Shelburne AE Wolves | Shelburne CDRC | | |
| Nov 23-Nov 24 | Atom LL #1 - Pharmasave | Regional Silver Stick (9340) (Wasaga Beach, ON) |
| AE080 | Nov 23 2019 | 1:40 PM | Atom LL #2 - Tom Smith Chev Buick GMC | Oro Thunder | Oro | | |
| PC-GB71 | Nov 23 2019 | 2:05 PM | Peewee AE - Precision Auto | Collingwood AE3 Blackhawks | Penetanguishene Memorial Community Centre | | |
| BE086 | Nov 23 2019 | 3:15 PM | Bantam LL - Hindson Marina | Coldwater Wildcats 2 | Penetanguishene Memorial Community Centre | | |
| MNH095 | Nov 23 2019 | 4:00 PM | Novice LL - Scotiabank | Elmvale Coyotes LL | Elmvale | | |
| MNH094 | Nov 23 2019 | 4:00 PM | Novice Rep - Bourgeois Nissan | Elmvale Coyotes | Elmvale | | |
| MB-GB35 | Nov 23 2019 | 4:35 PM | Midget AE - Olympia Sports | Wasaga Beach Stars | Penetanguishene Memorial Community Centre | | |
| MPS-AT-53 | Nov 23 2019 | 5:45 PM | Atom Rep - Asselin Insurance | Parry Sound Shamrocks | BOCC | | |
| BC-GB36 | Nov 23 2019 | 6:15 PM | Bantam AE - Royal Canadian Legion | Owen Sound AE Jr. Attack | Bayshore | | |
| MPS-PW-45 | Nov 23 2019 | 7:00 PM | Peewee Rep - Penetang Sand & Gravel | Parry Sound Shamrocks | BOCC | | |
| MNH101 | Nov 24 2019 | 3:00 PM | Novice Rep - Bourgeois Nissan | Essa Eagles | Penetanguishene Memorial Community Centre | | |
| MNH102 | Nov 24 2019 | 3:00 PM | Novice LL - Scotiabank | Essa Eagles LL | Penetanguishene Memorial Community Centre | | |
| PC-GB68 | Nov 24 2019 | 4:10 PM | Peewee AE - Precision Auto | Dundalk Storm | Penetanguishene Memorial Community Centre | | |
| BE088 | Nov 24 2019 | 5:20 PM | Bantam LL - Hindson Marina | Midland Centennials 1 | Penetanguishene Memorial Community Centre | | |
| BC-GB31 | Nov 24 2019 | 5:45 PM | Bantam AE - Royal Canadian Legion | Owen Sound AE Jr. Attack | JMRRC (2 - East) | | |
| PA-GB22 | Nov 25 2019 | 7:30 PM | Peewee Rep - Penetang Sand & Gravel | Midland Centennials | North Simcoe SRC (Centennial) | | |
| BC-GB23 | Nov 26 2019 | 8:00 PM | Bantam AE - Royal Canadian Legion | Orillia AE Terriers | Brian Orser | | |
| PE62 | Nov 28 2019 | 7:10 PM | Peewee LL - Scotiabank | Oro Thunder | Penetanguishene Memorial Community Centre | | |
| Nov 29-Dec 01 | Bantam LL - Hindson Marina | Hespeler Classic Hockey Tournament (8978) (Cambridge, ON) |
| PC-GB34 | Nov 29 2019 | 7:30 PM | Peewee AE - Precision Auto | Essa AE Eagles | Angus Rec | | |
| Nov 29 2019 | 8:00 PM | Penetang Jr. C Kings | Orillia Terriers | Penetanguishene Memorial Community Centre | | |
| Nov 30 2019 | 11:55 AM | Minor Novice - Tim Hortons | Coldwater Wildcats | Penetanguishene Memorial Community Centre | | |
| MNH109 | Nov 30 2019 | 12:55 PM | Novice Rep - Bourgeois Nissan | Collingwood Blackhawks | Penetanguishene Memorial Community Centre | | |
| MNH110 | Nov 30 2019 | 12:55 PM | Novice LL - Scotiabank | Collingwood Blackhawks LL | Penetanguishene Memorial Community Centre | | |
| AA-GB32 | Nov 30 2019 | 2:05 PM | Atom Rep - Asselin Insurance | Elmvale Coyotes | Penetanguishene Memorial Community Centre | | |
| AE100 | Nov 30 2019 | 3:15 PM | Atom LL #2 - Tom Smith Chev Buick GMC | Atom LL #1 - Pharmasave | Penetanguishene Memorial Community Centre | | |
| BA-GB70 | Nov 30 2019 | 4:25 PM | Bantam Rep - Paul Watson Esso | South Muskoka Bears | Penetanguishene Memorial Community Centre | | |
| MB-GB52 | Nov 30 2019 | 5:55 PM | Midget AE - Olympia Sports | South Muskoka Bears AE | Penetanguishene Memorial Community Centre | | |
| MA-GB48 | Nov 30 2019 | 7:10 PM | Midget Rep - Maloney Air | Oro Thunder | Oro | | |
| AA-GB38 | Dec 01 2019 | 3:00 PM | Atom Rep - Asselin Insurance | Elmvale Coyotes | Penetanguishene Memorial Community Centre | | |
| MNH015 | Dec 01 2019 | 3:10 PM | Novice LL - Scotiabank | South Muskoka Bears | Gravenhurst | | |
| MNH017 | Dec 01 2019 | 3:10 PM | Novice Rep - Bourgeois Nissan | South Muskoka Bears | Gravenhurst | | |
| PC-GB03 | Dec 01 2019 | 3:30 PM | Peewee AE - Precision Auto | Collingwood AE4 Blackhawks | Collingwood Central Park Arena | | |
| AE007 | Dec 01 2019 | 4:00 PM | Atom LL #2 - Tom Smith Chev Buick GMC | Coldwater Wildcats 1 | Coldwater | | |
| PE63 | Dec 01 2019 | 4:10 PM | Peewee LL - Scotiabank | Oro Thunder | Penetanguishene Memorial Community Centre | | |
| PA-GB14 | Dec 01 2019 | 4:15 PM | Peewee Rep - Penetang Sand & Gravel | Elmvale Coyotes | Elmvale | | |
| BA-GB43 | Dec 01 2019 | 5:20 PM | Bantam Rep - Paul Watson Esso | Oro Thunder | Oro | | |
| MB-GB37 | Dec 01 2019 | 5:20 PM | Midget AE - Olympia Sports | Owen Sound AE Jr. Attack | Penetanguishene Memorial Community Centre | | |
| MA-GB55 | Dec 01 2019 | 7:00 PM | Midget Rep - Maloney Air | Elmvale Coyotes | Penetanguishene Memorial Community Centre | | |
| ME29 | Dec 01 2019 | 8:30 PM | Midget LL - Sponsor TBD | Elmvale Coyotes 2 | Elmvale | | |
| AA-GB20 | Dec 02 2019 | 6:30 PM | Atom Rep - Asselin Insurance | Midland Centennials | North Simcoe SRC (Centennial) | | |
| BC-GB09 | Dec 03 2019 | 8:10 PM | Bantam AE - Royal Canadian Legion | Collingwood AE Blackhawks | Collingwood Central Park Arena | | |
| Dec 05-Dec 08 | Midget AE - Olympia Sports | Regional Silver Stick (Ayr, ON) |
| MNH120 | Dec 05 2019 | 5:45 PM | Novice LL - Scotiabank | Midland Centennials LL | North Simcoe SRC (Centennial) | | |
| MNH119 | Dec 05 2019 | 5:45 PM | Novice Rep - Bourgeois Nissan | Midland Centennials | North Simcoe SRC (Centennial) | | |
| Dec 06-Dec 08 | Midget Rep - Maloney Air | Bobby Orr Hall of Fame Tournament (9206) (Parry Sound, ON) |
| Dec 06-Dec 08 | Atom LL #2 - Tom Smith Chev Buick GMC | Richard Vollmer Memorial LL Tournament (9332) (Twin Centre, ON) |
| Dec 06-Dec 08 | Atom Rep - Asselin Insurance | Randy Merten / Dan Holland Memorial Tournament (9022) (Belle River, ON) |
| Dec 06 2019 | 8:00 PM | Penetang Jr. C Kings | Schomberg Cougars | Penetanguishene Memorial Community Centre | | |
| Dec 07-Dec 08 | Peewee Rep - Penetang Sand & Gravel | Regional Silver Stick (Wasaga Beach, ON) |
| Dec 07 2019 | 10:00 AM | Minor Novice - Tim Hortons | Clearview Canucks 1 | Stayner | | |
| Dec 07 2019 | 10:00 AM | Minor Novice - Tim Hortons | Clearview Canucks 2 | Stayner | | |
| BE007 | Dec 07 2019 | 11:00 AM | Bantam LL - Hindson Marina | Coldwater Wildcats 1 | Coldwater | | |
| AE059 | Dec 07 2019 | 12:30 PM | Atom LL #1 - Pharmasave | Midland Centennials 2 | North Simcoe SRC (Centennial) | | |
| MNH009 | Dec 07 2019 | 1:55 PM | Novice Rep - Bourgeois Nissan | South Muskoka Bears | Penetanguishene Memorial Community Centre | | |
| MNH010 | Dec 07 2019 | 1:55 PM | Novice LL - Scotiabank | South Muskoka Bears | Penetanguishene Memorial Community Centre | | |
| PE65 | Dec 07 2019 | 3:05 PM | Peewee LL - Scotiabank | Essa Eagles | Penetanguishene Memorial Community Centre | | |
| PC-GB69 | Dec 07 2019 | 4:15 PM | Peewee AE - Precision Auto | Owen Sound AE Jr. Attack | Penetanguishene Memorial Community Centre | | |
| BC-GB45 | Dec 07 2019 | 5:25 PM | Bantam AE - Royal Canadian Legion | Elmvale AE Coyotes | Penetanguishene Memorial Community Centre | | |
| BA-GB49 | Dec 07 2019 | 6:55 PM | Bantam Rep - Paul Watson Esso | Clearview Canucks | Penetanguishene Memorial Community Centre | | |
| ME90 | Dec 07 2019 | 8:25 PM | Midget LL - Sponsor TBD | Coldwater Wildcats 1 | Penetanguishene Memorial Community Centre | | |
| Dec 08 2019 | 2:00 PM | Minor Novice - Tim Hortons | Elmvale Coyotes 1 | Penetanguishene Memorial Community Centre | | |
| Dec 08 2019 | 2:00 PM | Minor Novice - Tim Hortons | Elmvale Coyotes 2 | Penetanguishene Memorial Community Centre | | |
| Dec 08 2019 | 3:00 PM | Novice LL - Scotiabank | Elmvale Coyotes LL | Penetanguishene Memorial Community Centre | | |
| Dec 08 2019 | 3:00 PM | Novice Rep - Bourgeois Nissan | Elmvale Coyotes | Penetanguishene Memorial Community Centre | | |
| AE021 | Dec 08 2019 | 3:00 PM | Atom LL #1 - Pharmasave | Coldwater Wildcats 3 | Coldwater | | |
| PE68 | Dec 08 2019 | 4:10 PM | Peewee LL - Scotiabank | Coldwater Wildcats 1 | Penetanguishene Memorial Community Centre | | |
| BE083 | Dec 08 2019 | 5:20 PM | Bantam LL - Hindson Marina | Midland Centennials 2 | Penetanguishene Memorial Community Centre | | |
| PC-GB22 | Dec 08 2019 | 5:55 PM | Peewee AE - Precision Auto | Elmvale AE Coyotes | Elmvale | | |
| BC-GB44 | Dec 08 2019 | 6:40 PM | Bantam AE - Royal Canadian Legion | Wasaga Beach Stars | Penetanguishene Memorial Community Centre | | |
| ME91 | Dec 08 2019 | 8:10 PM | Midget LL - Sponsor TBD | Coldwater Wildcats 2 | Penetanguishene Memorial Community Centre | | |
| PA-GB42 | Dec 09 2019 | 7:30 PM | Peewee Rep - Penetang Sand & Gravel | Shelburne Wolves | Shelburne CDRC | | |
| PC-GB90 | Dec 13 2019 | 7:30 PM | Peewee AE - Precision Auto | South Muskoka Bears AE | Penetanguishene Memorial Community Centre | | |
| ME92 | Dec 13 2019 | 8:40 PM | Midget LL - Sponsor TBD | Elmvale Coyotes 1 | Penetanguishene Memorial Community Centre | | |
| Dec 14-Dec 14 | Novice Rep - Bourgeois Nissan | Jamboree - Bob Merkley Memorial Regional Silver Stick (9333) (Midland, ON) |
| Dec 14-Dec 15 | Bantam Rep - Paul Watson Esso | Regional Silver Stick (Wasaga Beach, ON) |
| Dec 14-Dec 15 | Midget Rep - Maloney Air | Regional Silver Stick (Wasaga Beach, ON) |
| Dec 14 2019 | 1:40 PM | Minor Novice - Tim Hortons | Oro Thunder 2 | Oro | | |
| Dec 14 2019 | 1:40 PM | Minor Novice - Tim Hortons | Oro Thunder 1 | Oro | | |
| PE59 | Dec 14 2019 | 2:05 PM | Peewee LL - Scotiabank | Essa Eagles | Penetanguishene Memorial Community Centre | | |
| AA-GB36 | Dec 14 2019 | 3:15 PM | Atom Rep - Asselin Insurance | Midland Centennials | Penetanguishene Memorial Community Centre | | |
| MB-GB30 | Dec 14 2019 | 3:45 PM | Midget AE - Olympia Sports | Owen Sound AE Jr. Attack | Bayshore | | |
| AE092 | Dec 14 2019 | 4:25 PM | Atom LL #1 - Pharmasave | Atom LL #2 - Tom Smith Chev Buick GMC | Penetanguishene Memorial Community Centre | | |
| PA-GB32 | Dec 14 2019 | 5:35 PM | Peewee Rep - Penetang Sand & Gravel | Midland Centennials | Penetanguishene Memorial Community Centre | | |
| Dec 14 2019 | 8:00 PM | Penetang Jr. C Kings | Midland Flyers | Penetanguishene Memorial Community Centre | | |
| AA-GB30 | Dec 15 2019 | 1:10 PM | Atom Rep - Asselin Insurance | Oro Thunder | Oro | | |
| Dec 15 2019 | 2:00 PM | Minor Novice - Tim Hortons | Wasaga Beach Stars 1 | Penetanguishene Memorial Community Centre | | |
| Dec 15 2019 | 2:00 PM | Minor Novice - Tim Hortons | Wasaga Beach Stars 2 | Penetanguishene Memorial Community Centre | | |
| MNH146 | Dec 15 2019 | 3:00 PM | Novice LL - Scotiabank | Coldwater Wildcats | Coldwater | | |
| MNH147 | Dec 15 2019 | 3:00 PM | Novice Rep - Bourgeois Nissan | Midland Centennials | Penetanguishene Memorial Community Centre | | |
| PA-GB26 | Dec 15 2019 | 3:30 PM | Peewee Rep - Penetang Sand & Gravel | Oro Thunder | Oro | | |
| AE106 | Dec 15 2019 | 4:10 PM | Atom LL #2 - Tom Smith Chev Buick GMC | Coldwater Wildcats 2 | Penetanguishene Memorial Community Centre | | |
| PC-GB66 | Dec 15 2019 | 5:20 PM | Peewee AE - Precision Auto | Elmvale AE Coyotes | Penetanguishene Memorial Community Centre | | |
| BC-GB40 | Dec 15 2019 | 6:30 PM | Bantam AE - Royal Canadian Legion | Essa Eagles | Penetanguishene Memorial Community Centre | | |
| ME93 | Dec 15 2019 | 8:00 PM | Midget LL - Sponsor TBD | Elmvale Coyotes 2 | Penetanguishene Memorial Community Centre | | |
| Dec 20 2019 | 8:00 PM | Penetang Jr. C Kings | Midland Flyers | Penetanguishene Memorial Community Centre | | |
| BE031 | Dec 20 2019 | 8:40 PM | Bantam LL - Hindson Marina | Essa Eagles | Angus Rec | | |
| Dec 21 2019 | 9:00 AM | Minor Novice - Tim Hortons | Midland Centennials 1 | North Simcoe SRC (Centennial) | | |
| Dec 21 2019 | 9:00 AM | Minor Novice - Tim Hortons | Midland Centennials 2 | North Simcoe SRC (Centennial) | | |
| AA-GB35 | Dec 21 2019 | 12:55 PM | Atom Rep - Asselin Insurance | Collingwood Blackhawks | Penetanguishene Memorial Community Centre | | |
| PE06 | Dec 21 2019 | 1:15 PM | Peewee LL - Scotiabank | Coldwater Wildcats 1 | Coldwater | | |
| PC-GB72 | Dec 21 2019 | 2:05 PM | Peewee AE - Precision Auto | Oro AE Thunder | Penetanguishene Memorial Community Centre | | |
| PA-GB33 | Dec 21 2019 | 3:15 PM | Peewee Rep - Penetang Sand & Gravel | Collingwood Blackhawks | Penetanguishene Memorial Community Centre | | |
| AE095 | Dec 21 2019 | 4:30 PM | Atom LL #1 - Pharmasave | Coldwater Wildcats 3 | Penetanguishene Memorial Community Centre | | |
| BA-GB52 | Dec 21 2019 | 5:40 PM | Bantam Rep - Paul Watson Esso | Elmvale Coyotes | Penetanguishene Memorial Community Centre | | |
| ME40 | Dec 21 2019 | 6:50 PM | Midget LL - Sponsor TBD | Midland Centennials 1 | North Simcoe SRC (Centennial) | | |
| MB-GB38 | Dec 21 2019 | 7:10 PM | Midget AE - Olympia Sports | Shelburne AE Wolves | Penetanguishene Memorial Community Centre | | |
| MA-GB90 | Dec 21 2019 | 8:50 PM | Midget Rep - Maloney Air | South Muskoka Bears | Penetanguishene Memorial Community Centre | | |
| PC-GB49 | Dec 22 2019 | 11:50 AM | Peewee AE - Precision Auto | Oro AE Thunder | Oro | | |
| Dec 22 2019 | 2:00 PM | Minor Novice - Tim Hortons | Collingwood Blackhawks 1 | Penetanguishene Memorial Community Centre | | |
| Dec 22 2019 | 2:00 PM | Minor Novice - Tim Hortons | Collingwood Blackhawks 2 | Penetanguishene Memorial Community Centre | | |
| AE031 | Dec 22 2019 | 2:25 PM | Atom LL #1 - Pharmasave | Elmvale Coyotes 1 | Elmvale | | |
| AE099 | Dec 22 2019 | 3:00 PM | Atom LL #2 - Tom Smith Chev Buick GMC | Wasaga Beach Stars 1 | Penetanguishene Memorial Community Centre | | |
| PA-GB37 | Dec 22 2019 | 4:10 PM | Peewee Rep - Penetang Sand & Gravel | Shelburne Wolves | Penetanguishene Memorial Community Centre | | |
| AA-GB10 | Dec 22 2019 | 4:40 PM | Atom Rep - Asselin Insurance | Collingwood Blackhawks | Collingwood Central Park Arena | | |
| ME94 | Dec 22 2019 | 5:25 PM | Midget LL - Sponsor TBD | Midland Centennials 1 | Penetanguishene Memorial Community Centre | | |
| MA-GB51 | Dec 22 2019 | 6:45 PM | Midget Rep - Maloney Air | Flesherton Golden Hawks | Penetanguishene Memorial Community Centre | | |
| MA-GB75 | Dec 22 2019 | 9:10 PM | Midget AE - Olympia Sports | Wasaga Beach Stars | Wasaga | | |
| Dec 27 2019 | 8:00 PM | Penetang Jr. C Kings | Stayner Siskins | Penetanguishene Memorial Community Centre | | |
| MB-GB36 | Dec 28 2019 | 5:30 PM | Midget AE - Olympia Sports | Georgian Shores Lightning | Penetanguishene Memorial Community Centre | | |
| MA-GB21 | Dec 28 2019 | 6:15 PM | Midget Rep - Maloney Air | Elmvale Coyotes | Elmvale | | |
| PE23 | Dec 29 2019 | 4:45 PM | Peewee LL - Scotiabank | Elmvale Coyotes | Elmvale | | |
| MA-GB49 | Dec 29 2019 | 7:00 PM | Midget Rep - Maloney Air | Clearview Canucks | Penetanguishene Memorial Community Centre | | |
| ME80 | Dec 29 2019 | 7:10 PM | Midget LL - Sponsor TBD | Oro Thunder 3 | Oro | | |
| MNH169 | Jan 02 2020 | 5:45 PM | Novice LL - Scotiabank | Midland Centennials LL | North Simcoe SRC (Centennial) | | |
| MNH168 | Jan 02 2020 | 5:45 PM | Novice Rep - Bourgeois Nissan | Midland Centennials | North Simcoe SRC (Centennial) | | |
| Jan 03-Jan 05 | Midget AE - Olympia Sports | Winter Challenge (9044) (Fort Erie, ON) |
| Jan 03 2020 | 8:00 PM | Penetang Jr. C Kings | Orillia Terriers | Penetanguishene Memorial Community Centre | | |
| Jan 04 2020 | 11:00 AM | Minor Novice - Tim Hortons | Coldwater Wildcats | Coldwater | | |
| AE006 | Jan 04 2020 | 12:00 PM | Atom LL #1 - Pharmasave | Coldwater Wildcats 1 | Coldwater | | |
| AA-GB33 | Jan 04 2020 | 12:55 PM | Atom Rep - Asselin Insurance | Oro Thunder | Penetanguishene Memorial Community Centre | | |
| PC-GB67 | Jan 04 2020 | 2:05 PM | Peewee AE - Precision Auto | Midland AE Centennials | Penetanguishene Memorial Community Centre | | |
| PA-GB35 | Jan 04 2020 | 3:15 PM | Peewee Rep - Penetang Sand & Gravel | Collingwood Blackhawks | Penetanguishene Memorial Community Centre | | |
| BC-GB46 | Jan 04 2020 | 4:30 PM | Bantam AE - Royal Canadian Legion | Collingwood AE Blackhawks | Penetanguishene Memorial Community Centre | | |
| BA-GB54 | Jan 04 2020 | 6:00 PM | Bantam Rep - Paul Watson Esso | Collingwood Blackhawks | Penetanguishene Memorial Community Centre | | |
| MA-GB50 | Jan 04 2020 | 7:30 PM | Midget Rep - Maloney Air | Collingwood Blackhawks | Penetanguishene Memorial Community Centre | | |
| BE103 | Jan 04 2020 | 7:40 PM | Bantam LL - Hindson Marina | Wasaga Beach Stars 2 | Wasaga | | |
| ME95 | Jan 04 2020 | 9:10 PM | Midget LL - Sponsor TBD | Midland Centennials 2 | Penetanguishene Memorial Community Centre | | |
| Jan 05 2020 | 2:00 PM | Minor Novice - Tim Hortons | Midland Centennials 1 | Penetanguishene Memorial Community Centre | | |
| PC-GB45 | Jan 05 2020 | 2:00 PM | Peewee AE - Precision Auto | Midland AE Centennials | North Simcoe SRC (Centennial) | | |
| Jan 05 2020 | 2:00 PM | Minor Novice - Tim Hortons | Midland Centennials 2 | Penetanguishene Memorial Community Centre | | |
| AE101 | Jan 05 2020 | 3:00 PM | Atom LL #2 - Tom Smith Chev Buick GMC | Oro Thunder | Penetanguishene Memorial Community Centre | | |
| AE014 | Jan 05 2020 | 3:00 PM | Atom LL #1 - Pharmasave | Coldwater Wildcats 2 | Coldwater | | |
| AA-GB02 | Jan 05 2020 | 3:30 PM | Atom Rep - Asselin Insurance | Collingwood Blackhawks | Collingwood (Eddie Bush) Arena | | |
| PE13 | Jan 05 2020 | 4:00 PM | Peewee LL - Scotiabank | Coldwater Wildcats 2 | Coldwater | | |
| PA-GB36 | Jan 05 2020 | 4:10 PM | Peewee Rep - Penetang Sand & Gravel | Elmvale Coyotes | Penetanguishene Memorial Community Centre | | |
| BA-GB36 | Jan 05 2020 | 4:40 PM | Bantam Rep - Paul Watson Esso | Midland Centennials | North Simcoe SRC (Centennial) | | |
| MA-GB53 | Jan 05 2020 | 5:25 PM | Midget Rep - Maloney Air | Oro Thunder | Penetanguishene Memorial Community Centre | | |
| ME10 | Jan 05 2020 | 6:30 PM | Midget LL - Sponsor TBD | Coldwater Wildcats 2 | Coldwater | | |
| Jan 10-Jan 12 | Midget LL - Sponsor TBD | Bradford Blue & Gold (Bradford, ON) |
| Jan 10-Jan 12 | Bantam AE - Royal Canadian Legion | Aylmer AE Tournament (9215) (Aylmer, ON) |
| Jan 10 2020 | 8:00 PM | Penetang Jr. C Kings | Huntsville Otters | Penetanguishene Memorial Community Centre | | |
| AE104 | Jan 11 2020 | 12:55 PM | Atom LL #2 - Tom Smith Chev Buick GMC | Elmvale Coyotes 1 | Penetanguishene Memorial Community Centre | | |
| PE43 | Jan 11 2020 | 1:40 PM | Peewee LL - Scotiabank | Midland Centennials | North Simcoe SRC (Centennial) | | |
| Jan 12 2020 | 2:00 PM | Minor Novice - Tim Hortons | Oro Thunder 2 | Penetanguishene Memorial Community Centre | | |
| Jan 12 2020 | 2:00 PM | Minor Novice - Tim Hortons | Oro Thunder 1 | Penetanguishene Memorial Community Centre | | |
| AE039 | Jan 12 2020 | 3:35 PM | Atom LL #2 - Tom Smith Chev Buick GMC | Elmvale Coyotes 2 | Elmvale | | |
| PE61 | Jan 12 2020 | 5:20 PM | Peewee LL - Scotiabank | Wasaga Beach Stars 1 | Penetanguishene Memorial Community Centre | | |
| Jan 17-Jan 19 | Atom LL #1 - Pharmasave | Frank Sabatino Memorial (Oakville, ON) |
| Jan 17 2020 | 8:00 PM | Penetang Jr. C Kings | Schomberg Cougars | Penetanguishene Memorial Community Centre | | |
| AE068 | Jan 18 2020 | 11:20 AM | Atom LL #2 - Tom Smith Chev Buick GMC | Midland Centennials 3 | North Simcoe SRC (Centennial) | | |
| PE72 | Jan 18 2020 | 3:40 PM | Peewee LL - Scotiabank | Wasaga Beach Stars 1 | Wasaga | | |
| BE091 | Jan 18 2020 | 6:20 PM | Bantam LL - Hindson Marina | Wasaga Beach Stars 1 | Wasaga | | |
| AE058 | Jan 19 2020 | 1:50 PM | Atom LL #2 - Tom Smith Chev Buick GMC | Midland Centennials 2 | North Simcoe SRC (Centennial) | | |
| BE087 | Jan 19 2020 | 5:20 PM | Bantam LL - Hindson Marina | Coldwater Wildcats 1 | Penetanguishene Memorial Community Centre | | |
| ME23 | Jan 19 2020 | 8:30 PM | Midget LL - Sponsor TBD | Elmvale Coyotes 1 | Elmvale | | |
| Jan 24-Jan 26 | Atom Rep - Asselin Insurance | International Silver Stick (Forest, ON) |
| Jan 24 2020 | 8:00 PM | Penetang Jr. C Kings | Caledon Golden Hawks | Penetanguishene Memorial Community Centre | | |
| Jan 25-Jan 25 | Novice LL - Scotiabank | Novice LL Coldwater Tournament (Coldwater, ON) |
| Jan 25 2020 | 9:00 AM | Minor Novice - Tim Hortons | Collingwood Blackhawks 1 | Collingwood Central Park Arena | | |
| Jan 25 2020 | 9:00 AM | Minor Novice - Tim Hortons | Collingwood Blackhawks 2 | Collingwood Central Park Arena | | |
| AE069 | Jan 25 2020 | 4:10 PM | Atom LL #1 - Pharmasave | Midland Centennials 3 | North Simcoe SRC (MMHA) | | |
| BE070 | Jan 25 2020 | 5:40 PM | Bantam LL - Hindson Marina | Oro Thunder 2 | Oro | | |
| ME69 | Jan 26 2020 | 7:10 PM | Midget LL - Sponsor TBD | Oro Thunder 2 | Oro | | |
| Jan 31 2020 | 8:00 PM | Penetang Jr. C Kings | Caledon Golden Hawks | Penetanguishene Memorial Community Centre | | |
| Feb 01-Feb 01 | Atom LL #2 - Tom Smith Chev Buick GMC | Midland Canadian Tire Winterfest Tournament (9380) (Midland, ON) |
| Feb 01-Feb 02 | Peewee LL - Scotiabank | Midland Winterfest (Midland, ON) |
| Feb 02 2020 | 2:00 PM | Minor Novice - Tim Hortons | Clearview Canucks 1 | Penetanguishene Memorial Community Centre | | |
| Feb 02 2020 | 2:00 PM | Minor Novice - Tim Hortons | Clearview Canucks 2 | Penetanguishene Memorial Community Centre | | |
| Feb 15-Feb 15 | Minor Novice - Tim Hortons | Shamrock Minor Novice Jamboree (Parry Sound) |
| Feb 21-Feb 23 | Bantam LL - Hindson Marina | Max Partlo Memorial LL Tournament (9164) (Tillsonburg, ON) |
| Feb 29 2020 | 3:00 PM | Minor Novice - Tim Hortons | Elmvale Coyotes 2 | Elmvale | | |
| Feb 29 2020 | 3:00 PM | Minor Novice - Tim Hortons | Elmvale Coyotes 1 | Elmvale | | |
| Mar 08 2020 | 12:00 PM | Minor Novice - Tim Hortons | Wasaga Beach Stars 1 | Wasaga | | |
| Mar 08 2020 | 12:00 PM | Minor Novice - Tim Hortons | Wasaga Beach Stars 2 | Wasaga | | |
| Mar 20-Mar 22 | Atom LL #2 - Tom Smith Chev Buick GMC | Knights of Columbus Annual Tournament (9484) (Huntsville, ON) |
| Mar 27-Mar 29 | Atom Rep - Asselin Insurance | Elmvale Maple Syrup Tournament (9251) (Elmvale, ON) |