All Competitions
| Game | Date ↑ | Time | Field | Home | Visitors | |
|---|---|---|---|---|---|---|
| C3 | Mon, May-15 | 8:15 pm | MikMac Field | Winmar FC | 1 - 4 | Brockville United FC |
| C7 | Mon, May-22 | 6:30 pm | Woodbine 5 | Jimmy's Sports Lounge SC | 1 - 3 | Winmar FC |
| C12 | Mon, May-29 | 6:30 pm | Woodbine 5 | Winmar FC | 3 - 2 | Athletic Kerala FC |
| N6 | Mon, Jun-05 | 6:30 pm | Barr Homes 2 | Independent FC | 1 - 2 | Winmar FC |
| C13 | Mon, Jun-12 | 6:30 pm | Woodbine 5 | Winmar FC | 2 - 3 | Riverhead Brewing FC |
| C18 | Mon, Jun-19 | 6:30 pm | MikMac Field | Remax United | 5 - 1 | Winmar FC |
| N11 | Fri, Jun-23 | 6:30 pm | Barr Homes 3 | Xtirpation FC | 2 - 2 | Winmar FC |
| Penalty Kicks | (5 - 4) | |||||
| C23 | Mon, Jun-26 | 6:30 pm | CaraCo Home Field | Winmar FC | 1 - 0 | Grizzly's |
| C26 | Mon, Jul-03 | 6:30 pm | CFB McNaughton | CFB Kingston Knights | 1 - 3 | Winmar FC |
| C31 | Mon, Jul-10 | 6:30 pm | Woodbine 5 | Grizzly's | 1 - 4 | Winmar FC |
| C35 | Mon, Jul-17 | 6:30 pm | Barr Homes 2 | Winmar FC | 3 - 1 | Jimmy's Sports Lounge SC |
| C40 | Mon, Jul-24 | 6:30 pm | CaraCo Home Field | Athletic Kerala FC | 0 - 1 | Winmar FC |
| C43 | Mon, Jul-31 | 8:15 pm | MikMac Field | Brockville United FC | 1 - 2 | Winmar FC |
| C46 | Mon, Aug-07 | 6:30 pm | Woodbine 5 | Winmar FC | 1 - 3 | Remax United |
| C49 | Mon, Aug-14 | 6:30 pm | CaraCo Home Field | Riverhead Brewing FC | 3 - 0 | Winmar FC |
| C54* (f) | Fri, Aug-18 | 6:00 pm | CFB McNaughton | Winmar FC | 3 - 0 | CFB Kingston Knights |
| C59* | Mon, Aug-28 | 6:00 pm | CFB Hospital | Winmar FC | 1 - 1 | CFB Kingston Knights |
| Penalty Kicks | (4 - 5) |