Winmar FC's cup games
| Game | Date ↑ | Time | Field | Home | Visitors | |
|---|---|---|---|---|---|---|
| N1 | Mon, May-30 | 6:30 pm | Barr Homes 3 | Riverhead Brewing FC | 1 - 2 | Independent FC |
| N2 | Mon, May-30 | 6:30 pm | Barr Homes 2 | Winmar FC | 4 - 0 | Tekenos-Levy Law |
| N3 | Mon, May-30 | 6:30 pm | CFB McNaughton | CFB Kingston Knights | 3 - 2 | Jimmy's Sports Lounge SC |
| N6 | Mon, May-30 | 6:30 pm | Woodbine 5 | King's Crew FC | 1 - 1 | Red House FC |
| Penalty Kicks | (4 - 5) | |||||
| N7 | Mon, May-30 | 6:30 pm | Caton's 1 | Remax United | 3 - 2 | Athletic Kerala FC |
| N4 | Mon, May-30 | 8:30 pm | CaraCo Home Field | Advantage Pools and Home | 3 - 1 | Grizzly's |
| N5 | Mon, May-30 | 8:30 pm | Catons 1 | First Responders FC | 3 - 1 | AIC |
| N8 | Mon, May-30 | 8:30 pm | Woodbine 5 | Xtirpation FC | 6 - 1 | JKL Rangers |
| L1 | Tue, May-31 | 6:30 pm | Barr Homes 2 | KUSC | 1 - 6 | Cataraqui FC |
| L2 | Tue, May-31 | 6:30 pm | Woodbine 5 | Scarpazza Homes | 0 - 0 | Portsmouth Celtic FC |
| Penalty Kicks | (4 - 3) | |||||
| L3 | Tue, May-31 | 6:30 pm | Barr Homes 3 | Glenhaven United | 2 - 2 | Green Wave Legacy FC |
| Penalty Kicks | (2 - 3) | |||||
| N10* | Fri, Jun-24 | 6:30 pm | CFB McNaughton | CFB Kingston Knights | 1 - 5 | Advantage Pools and Home |
| N9* | Thu, Jul-07 | 6:30 pm | Barr Homes 2 | Independent FC | 0 - 5 | Winmar FC |
| N11 | Fri, Jul-08 | 6:30 pm | Barr Homes 2 | First Responders FC | 2 - 3 | Red House FC |
| N12 | Fri, Jul-08 | 6:30 pm | Barr Homes 3 | Remax United | 2 - 1 | Xtirpation FC |
| L4* (f) | Fri, Jul-15 | 6:30 pm | Barr Homes 3 | Portuguese Benfica | 3 - 3 | Cataraqui FC |
| Penalty Kicks | (3 - 1) | |||||
| L5* | Fri, Jul-22 | 6:30 pm | Barr Homes 4 | Boca Nooners | 2 - 2 | Scarpazza Homes |
| Penalty Kicks | (4 - 5) | |||||
| L6 | Fri, Jul-22 | 6:30 pm | Barr Homes 2 | Valhalla | 3 - 0 | Green Wave Legacy FC |
| L7 | Fri, Jul-22 | 6:30 pm | Barr Homes 3 | Limestone City FC | 3 - 2 | Hotfire |
| N13 | Fri, Aug-05 | 6:00 pm | Barr Homes 3 | Winmar FC | 2 - 1 | Advantage Pools and Home |
| N14 | Fri, Aug-05 | 6:00 pm | Barr Homes 2 | Red House FC | 0 - 1 | Remax United |
| L8 | Fri, Aug-12 | 6:00 pm | Barr Homes 3 | Cataraqui FC | 1 - 2 | Scarpazza Homes |
| L9 | Fri, Aug-12 | 6:00 pm | Barr Homes 2 | Valhalla | 1 - 1 | Limestone City FC |
| Penalty Kicks | (3 - 4) | |||||
| N15* | Sun, Sep-25 | 1:00 pm | Barr Homes 3 | Winmar FC | 2 - 1 | Remax United |
| L10* | Sun, Sep-25 | 3:00 pm | Barr Homes 3 | Scarpazza Homes | 1 - 3 | Limestone City FC |