| 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 | | |
| 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 | | |
| 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 | | |
| 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 | | |
| 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 | | |
| Sep 21 2019 | 6:35 PM | Bantam AE - Royal Canadian Legion | Collingwood Blackhawks AE | Penetanguishene Memorial Community Centre | | |
| Sep 21 2019 | 8:15 PM | Midget AE - Koppenol Auto | South Muskoka Bears AE | Penetanguishene Memorial Community Centre | | |
| 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 | | |
| 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 | | |
| 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 | | |
| Sep 29 2019 | 5:45 PM | Bantam Rep - Paul Watson Esso | Huntsville Otters | Penetanguishene Memorial Community Centre | | |
| MPS-BT-44 | Oct 05 2019 | 1:10 PM | Bantam AE - Royal Canadian Legion | Huntsville Otters AE | CSC (Don Lough) | | |
| MPS-PW-26 | Oct 05 2019 | 1:40 PM | Peewee Rep - Penetang Sand & Gravel | Huntsville Otters | CSC (Jack Bionda) | | |
| Oct 05 2019 | 2:05 PM | Peewee AE - Precision Auto | Muskoka Rock | Penetanguishene Memorial Community Centre | | |
| MPS-BT-43 | Oct 05 2019 | 3:00 PM | Bantam Rep - Paul Watson Esso | Huntsville Otters | CSC (Don Lough) | | |
| Oct 05 2019 | 5:35 PM | Midget AE - Koppenol Auto | Huntsville Otters AE | Penetanguishene Memorial Community Centre | | |
| MPS-MD-33 | Oct 05 2019 | 7:10 PM | Midget Rep - Maloney Air | Huntsville Otters | CSC (Don Lough) | | |
| Oct 05 2019 | 8:00 PM | Penetang Jr. C Kings | Alliston Hornets | Penetanguishene Memorial Community Centre | | |
| MPS-MD-76 | Oct 06 2019 | 3:00 PM | Midget AE - Koppenol Auto | South Muskoka Bears AE | Bracebridge | | |
| AA-GB40 | Oct 06 2019 | 3:00 PM | Atom Rep - Asselin Insurance | Parry Sound Shamrocks | Penetanguishene Memorial Community Centre | | |
| Oct 06 2019 | 5:20 PM | Peewee Rep - Penetang Sand & Gravel | Parry Sound Shamrocks | Penetanguishene Memorial Community Centre | | |
| Oct 11 2019 | 8:00 PM | Penetang Jr. C Kings | Huntsville Otters | Penetanguishene Memorial Community Centre | | |
| AA-GB41 | Oct 12 2019 | 2:05 PM | Atom Rep - Asselin Insurance | South Muskoka Bears | Penetanguishene Memorial Community Centre | | |
| MPS-PW-56 | Oct 12 2019 | 4:00 PM | Peewee Rep - Penetang Sand & Gravel | South Muskoka Bears | Gravenhurst | | |
| MPS-PW-72 | Oct 12 2019 | 5:30 PM | Peewee AE - Precision Auto | South Muskoka Bears AE | Gravenhurst | | |
| Oct 12 2019 | 7:00 PM | Bantam Rep - Paul Watson Esso | Parry Sound Shamrocks | Penetanguishene Memorial Community Centre | | |
| Oct 12 2019 | 8:30 PM | Midget Rep - Maloney Air | Parry Sound Shamrocks | Penetanguishene Memorial Community Centre | | |
| 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 | | |
| AA-GB42 | Oct 19 2019 | 12:55 PM | Atom Rep - Asselin Insurance | Huntsville Otters | Penetanguishene Memorial Community Centre | | |
| Oct 25-Oct 27 | Atom Rep - Asselin Insurance | PEC Milk Tournament (8996) (Prince Edward County, ON) |
| Oct 25 2019 | 8:00 PM | Penetang Jr. C Kings | Caledon Golden Hawks | Penetanguishene Memorial Community Centre | | |
| Oct 26 2019 | 4:25 PM | Peewee Rep - Penetang Sand & Gravel | Huntsville Otters | Penetanguishene Memorial Community Centre | | |
| Oct 26 2019 | 7:10 PM | Bantam AE - Royal Canadian Legion | Huntsville Otters AE | Penetanguishene Memorial Community Centre | | |
| Oct 26 2019 | 8:30 PM | Midget Rep - Maloney Air | Huntsville Otters | Penetanguishene Memorial Community Centre | | |
| Nov 01-Nov 03 | Midget Rep - Maloney Air | Peter Mancuso November Challenge (9026) (Niagara Falls, ON) |
| Nov 01-Nov 03 | Midget AE - Koppenol Auto | Winston Watson Memorial Midget AE Tournament (9177) (Huntsville, ON) |
| Nov 01 2019 | 7:30 PM | Peewee Rep - Penetang Sand & Gravel | South Muskoka Bears | Penetanguishene Memorial Community Centre | | |
| Nov 02 2019 | 8:00 PM | Penetang Jr. C Kings | Alliston Hornets | Penetanguishene Memorial Community Centre | | |
| MPS-PW-41 | Nov 03 2019 | 4:30 PM | Peewee AE - Precision Auto | Muskoka Rock | Port Carling | | |
| MPS-BT-67 | Nov 03 2019 | 5:30 PM | Bantam Rep - Paul Watson Esso | Parry Sound Shamrocks | BOCC | | |
| 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 11 | Atom LL #2 - Tom Smith Chev Buick GMC | Regional Silver Stick (Collingwood, ON) |
| Nov 08 2019 | 8:00 PM | Penetang Jr. C Kings | Stayner Siskins | Penetanguishene Memorial Community Centre | | |
| MPS-AT-58 | Nov 09 2019 | 2:15 PM | Atom Rep - Asselin Insurance | South Muskoka Bears | Bracebridge | | |
| MPS-MD-41 | Nov 09 2019 | 7:10 PM | Midget AE - Koppenol Auto | Huntsville Otters AE | CSC (Don Lough) | | |
| MPS-AT-29 | Nov 10 2019 | 12:40 PM | Atom Rep - Asselin Insurance | Huntsville Otters | CSC (Jack Bionda) | | |
| MPS-BT-74 | Nov 10 2019 | 3:00 PM | Bantam Rep - Paul Watson Esso | South Muskoka Bears | Gravenhurst | | |
| 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 | | |
| Nov 16-Nov 17 | Atom Rep - Asselin Insurance | Regional Silver Stick (Wasaga Beach, 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 | | |
| Nov 23-Nov 24 | Atom LL #1 - Pharmasave | Regional Silver Stick (9340) (Wasaga Beach, ON) |
| MPS-AT-53 | Nov 23 2019 | 5:45 PM | Atom Rep - Asselin Insurance | Parry Sound Shamrocks | BOCC | | |
| MPS-PW-45 | Nov 23 2019 | 7:00 PM | Peewee Rep - Penetang Sand & Gravel | Parry Sound Shamrocks | BOCC | | |
| Nov 29-Dec 01 | Bantam AE - Royal Canadian Legion | Art Coombs Memorial Rep Tournament (9203) (Paris, ON) |
| Nov 29-Dec 01 | Bantam LL - Hindson Marina | Hespeler Classic Hockey Tournament (8978) (Cambridge, ON) |
| Nov 29 2019 | 8:00 PM | Penetang Jr. C Kings | Orillia Terriers | Penetanguishene Memorial Community Centre | | |
| Nov 30 2019 | 6:50 PM | Bantam Rep - Paul Watson Esso | South Muskoka Bears | Penetanguishene Memorial Community Centre | | |
| Nov 30 2019 | 8:30 PM | Midget AE - Koppenol Auto | South Muskoka Bears AE | Penetanguishene Memorial Community Centre | | |
| Dec 05-Dec 08 | Midget AE - Koppenol Auto | Regional Silver Stick (Ayr, ON) |
| Dec 06-Dec 08 | Midget Rep - Maloney Air | Bobby Orr Hall of Fame Tournament (9206) (Parry Sound, 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 13 2019 | 7:30 PM | Peewee AE - Precision Auto | South Muskoka Bears AE | 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 | 8:00 PM | Penetang Jr. C Kings | Midland Flyers | Penetanguishene Memorial Community Centre | | |
| Dec 20 2019 | 8:00 PM | Penetang Jr. C Kings | Midland Flyers | Penetanguishene Memorial Community Centre | | |
| Dec 21 2019 | 8:40 PM | Midget Rep - Maloney Air | South Muskoka Bears | Penetanguishene Memorial Community Centre | | |
| Dec 27 2019 | 8:00 PM | Penetang Jr. C Kings | Stayner Siskins | Penetanguishene Memorial Community Centre | | |
| Jan 03 2020 | 8:00 PM | Penetang Jr. C Kings | Orillia Terriers | Penetanguishene Memorial Community Centre | | |
| Jan 10 2020 | 8:00 PM | Penetang Jr. C Kings | Huntsville Otters | Penetanguishene Memorial Community Centre | | |
| Jan 17 2020 | 8:00 PM | Penetang Jr. C Kings | Schomberg Cougars | Penetanguishene Memorial Community Centre | | |
| Jan 24 2020 | 8:00 PM | Penetang Jr. C Kings | Caledon Golden Hawks | Penetanguishene Memorial Community Centre | | |
| Jan 31 2020 | 8:00 PM | Penetang Jr. C Kings | Caledon Golden Hawks | Penetanguishene Memorial Community Centre | | |
| Feb 21-Feb 23 | Bantam LL - Hindson Marina | Max Partlo Memorial LL Tournament (9164) (Tillsonburg, ON) |
| Mar 27-Mar 29 | Atom Rep - Asselin Insurance | Elmvale Maple Syrup Tournament (9251) (Elmvale, ON) |