All Competitions
| Game | Date ↑ | Time | Field | Home | Visitors | |
|---|---|---|---|---|---|---|
| C3 | Mon, May-23 | 6:30 pm | Woodbine 5 | Winmar FC | 7 - 0 | Independent FC |
| N2 | Mon, May-30 | 6:30 pm | Barr Homes 2 | Winmar FC | 4 - 0 | Tekenos-Levy Law |
| C7 | Mon, Jun-06 | 8:30 pm | CaraCo Home Field | Jimmy's Sports Lounge SC | 1 - 3 | Winmar FC |
| C12* | Mon, Jun-13 | 8:30 pm | Caton's 1 | Winmar FC | 2 - 5 | Athletic Kerala FC |
| C13* | Mon, Jun-20 | 6:30 pm | Caton's 1 | Winmar FC | 2 - 2 | Advantage Pools and Home |
| C18 | Mon, Jun-27 | 6:30 pm | Caton's 1 | Remax United | 1 - 3 | Winmar FC |
| C23 | Mon, Jul-04 | 6:30 pm | Barr Homes 3 | Winmar FC | 3 - 0 | Grizzly's |
| N9* | Thu, Jul-07 | 6:30 pm | Barr Homes 2 | Independent FC | 0 - 5 | Winmar FC |
| C26 | Mon, Jul-11 | 6:30 pm | CFB McNaughton | CFB Kingston Knights | 2 - 4 | Winmar FC |
| C35 | Mon, Jul-25 | 6:30 pm | Caton's 1 | Winmar FC | 3 - 2 | Jimmy's Sports Lounge SC |
| C40 | Mon, Aug-01 | 6:00 pm | Barr Homes 2 | Athletic Kerala FC | 0 - 4 | Winmar FC |
| N13 | Fri, Aug-05 | 6:00 pm | Barr Homes 3 | Winmar FC | 2 - 1 | Advantage Pools and Home |
| C43 | Mon, Aug-08 | 6:30 pm | Woodbine 5 | Grizzly's | 0 - 1 | Winmar FC |
| C46 | Mon, Aug-15 | 6:30 pm | Caton's 1 | Winmar FC | 3 - 0 | Remax United |
| C49 | Mon, Aug-22 | 6:30 pm | Woodbine 5 | Advantage Pools and Home | 1 - 1 | Winmar FC |
| C31* | Fri, Aug-26 | 6:00 pm | Barr Homes 3 | Independent FC | 2 - 5 | Winmar FC |
| C54* | Mon, Aug-29 | 6:00 pm | CFB McNaughton | Winmar FC | 0 - 0 | CFB Kingston Knights |
| C58 | Fri, Sep-09 | 6:15 pm | Woodbine 4 | Winmar FC | 3 - 1 | Remax United |
| C62 | Mon, Sep-12 | 8:15 pm | Woodbine 5 | Winmar FC | 2 - 2 | CFB Kingston Knights |
| Penalty Kicks | (4 - 3) | |||||
| C63 | Sun, Sep-18 | 12:00 pm | Barr Homes 3 | Advantage Pools and Home | 6 - 0 | Winmar FC |
| N15* | Sun, Sep-25 | 1:00 pm | Barr Homes 3 | Winmar FC | 2 - 1 | Remax United |