| Oct 1, 2023 | mjhl | Winnipeg Blues @ Winkler Flyers | 0–6 | 18 | Referee | Penner, Kile, Cramer |
| Sep 6, 2023 | mjhl | Steinbach Pistons @ Winkler Flyers | 5–1 | 20 | Referee | Powell, Matuszewski, Sibbald |
| Apr 2, 2023 | mjhl | Steinbach Pistons @ Winkler Flyers | 1–3 | 18 | Linesman | Gagnon, Rapsky, Cameron |
| Mar 15, 2023 | mjhl | Steinbach Pistons @ Winkler Flyers | 2–1 | 66 | Linesman | Peluk, Hofer, Street |
| Feb 8, 2023 | mjhl | Steinbach Pistons @ Winkler Flyers | 3–2 | 36 | Linesman | Croker, Gagnon, Paul |
| Feb 3, 2023 | mjhl | Winnipeg Blues @ Winkler Flyers | 1–4 | 18 | Linesman | Zacharias, Gramiak, Derksen |
| Jan 27, 2023 | mjhl | Neepawa Titans @ Winkler Flyers | 2–4 | 18 | Linesman | Wilkinson, Penner, Derksen |
| Jan 20, 2023 | mjhl | Winnipeg Blues @ Winkler Flyers | 4–5 | 42 | Referee | Derksen, Street |
| Jan 18, 2023 | mjhl | Portage Terriers @ Winkler Flyers | 4–3 | 56 | Linesman | Peluk, Powell, Derksen |
| Jan 4, 2023 | mjhl | Winnipeg Freeze @ Winkler Flyers | 0–3 | 44 | Linesman | Zacharias, Richardson |
| Dec 21, 2022 | mjhl | Portage Terriers @ Winkler Flyers | 3–1 | 54 | Linesman | Penner, Friesen, Derksen |
| Dec 2, 2022 | mjhl | Dauphin Kings @ Winkler Flyers | 1–3 | 79 | Linesman | Gramiak, Comte, Derksen |
| Nov 18, 2022 | mjhl | Waywayseecappo Wolverines @ Winkler Flyers | 1–4 | 44 | Linesman | Gauvin, Hofer |
| Nov 2, 2022 | mjhl | Steinbach Pistons @ Winkler Flyers | 4–1 | 12 | Referee | Penner, Derksen |
| Oct 22, 2022 | mjhl | Swan Valley Stampeders @ Winkler Flyers | 1–3 | 24 | Referee | Penner, Derksen |
| Oct 14, 2022 | mjhl | Winnipeg Freeze @ Winkler Flyers | 1–4 | 20 | Referee | Wilkinson, Street |
| Oct 12, 2022 | mjhl | Virden Oil Capitals @ Winkler Flyers | 4–5 | 50 | Referee | Mitchell, Derksen, Smith |
| Oct 2, 2022 | mjhl | Waywayseecappo Wolverines @ Winkler Flyers | 2–1 | 20 | Referee | Martens, Granger, Derksen |
| Sep 11, 2022 | mjhl | Selkirk Steelers @ Winkler Flyers | 2–1 | 66 | Referee | Martens, Wolfe, Hill |
| Sep 9, 2022 | mjhl | Steinbach Pistons @ Winkler Flyers | 0–6 | 32 | Referee | Martens, Derksen, Wolfe |
| Apr 3, 2022 | mjhl | Winnipeg Blues @ Winkler Flyers | 1–3 | 22 | Linesman | Penner, Friesen, Derksen |
| Mar 9, 2022 | mjhl | Winnipeg Blues @ Winkler Flyers | 2–3 | 58 | Linesman | MacDonald, Hofer, Hill |
| Mar 2, 2022 | mjhl | Selkirk Steelers @ Winkler Flyers | 4–4 | 48 | Linesman | Ginter, Hofer, Derksen |
| Feb 23, 2022 | mjhl | Selkirk Steelers @ Winkler Flyers | 2–1 | 12 | Linesman | Kielich, Friesen, Derksen |
| Feb 9, 2022 | mjhl | Steinbach Pistons @ Winkler Flyers | 4–1 | 22 | Linesman | Powell, Szczepanksi, Street |
