| Des Moines Menace vs WSA Winnipeg | 2019-05-24 07:30:25May 24, 2019 | Des Moines Menace vs WSA Winnipeg | 07:30:257:30 am | USL League 2 | 2019 | |
| Kaw Valley FC vs WSA Winnipeg | 2019-05-25 19:30:25May 25, 2019 | Kaw Valley FC vs WSA Winnipeg | 19:30:257:30 pm | USL League 2 | 2019 | |
| St.Louis Lions vs WSA Winnipeg | 2019-05-28 17:00:09May 28, 2019 | St.Louis Lions vs WSA Winnipeg | 17:00:095:00 pm | USL League 2 | 2019 | |
| Des Moines Menace vs WSA Winnipeg | 2019-05-30 19:30:27May 30, 2019 | Des Moines Menace vs WSA Winnipeg | 19:30:277:30 pm | USL League 2 | 2019 | |
| Green Bay Voyageurs vs WSA Winnipeg | 2019-05-31 19:00:29May 31, 2019 | Green Bay Voyageurs vs WSA Winnipeg | 19:00:297:00 pm | USL League 2 | 2019 | |
| Thunder Bay Chill vs WSA Winnipeg | 2019-06-07 19:30:29June 7, 2019 | Thunder Bay Chill vs WSA Winnipeg | 19:30:297:30 pm | USL League 2 | 2019 | |
| Thunder Bay Chill vs WSA Winnipeg | 2019-06-08 19:30:00June 8, 2019 | Thunder Bay Chill vs WSA Winnipeg | 19:30:007:30 pm | USL League 2 | 2019 | |
| WSA Winnipeg vs Thunder Bay Chill | 2019-06-14 19:00:01June 14, 2019 | WSA Winnipeg vs Thunder Bay Chill | 19:00:017:00 pm | USL League 2 | 2019 | Winnipeg Soccer Complex |
| WSA Winnipeg vs Thunder Bay Chill | 2019-06-15 19:00:18June 15, 2019 | WSA Winnipeg vs Thunder Bay Chill | 19:00:187:00 pm | USL League 2 | 2019 | Winnipeg Soccer Complex |
| WSA Winnipeg vs Des Moines Menace | 2019-06-24 19:00:12June 24, 2019 | WSA Winnipeg vs Des Moines Menace | 19:00:127:00 pm | USL League 2 | 2019 | Winnipeg Soccer Complex |
| WSA Winnipeg vs Des Moines Menace | 2019-06-25 19:00:30June 25, 2019 | WSA Winnipeg vs Des Moines Menace | 19:00:307:00 pm | USL League 2 | 2019 | Winnipeg Soccer Complex |
| WSA Winnipeg vs St.Louis Lions | 2019-06-29 19:00:16June 29, 2019 | WSA Winnipeg vs St.Louis Lions | 19:00:167:00 pm | USL League 2 | 2019 | Winnipeg Soccer Complex |
| WSA Winnipeg vs Green Bay Voyageurs | 2019-07-01 19:00:13July 1, 2019 | WSA Winnipeg vs Green Bay Voyageurs | 19:00:137:00 pm | USL League 2 | 2019 | Winnipeg Soccer Complex |
| WSA Winnipeg vs Kaw Valley FC | 2019-07-08 19:00:25July 8, 2019 | WSA Winnipeg vs Kaw Valley FC | 19:00:257:00 pm | USL League 2 | 2019 | Winnipeg Soccer Complex |
