| Mar 14, 2025 | mjhl | Winnipeg Freeze @ Winkler Flyers | 1–8 | 31 | Linesman | Mitchell, Hofer, Kile |
| Feb 19, 2025 | mjhl | Winnipeg Blues @ Winkler Flyers | 2–6 | 8 | Linesman | Letkeman, Penner, Street |
| Feb 4, 2025 | mjhl | Winnipeg Blues @ Winkler Flyers | 0–7 | 20 | Linesman | Powell, Hinds, Miko |
| Feb 1, 2025 | mjhl | Neepawa Titans @ Winkler Flyers | 2–3 | 28 | Linesman | Letkeman, Swedlo, Sibbald |
| Jan 5, 2025 | mjhl | Niverville Nighthawks @ Winkler Flyers | 2–5 | 54 | Linesman | Penner, Heide, Lyle |
| Dec 20, 2024 | mjhl | Steinbach Pistons @ Winkler Flyers | 2–5 | 24 | Linesman | Peluk, Zacharias, Loewen |
| Dec 1, 2024 | mjhl | Winnipeg Blues @ Winkler Flyers | 1–4 | 60 | Linesman | Burnell, Zacharias, Matuszewski |
| Nov 10, 2024 | mjhl | Virden Oil Capitals @ Winkler Flyers | 1–3 | 30 | Linesman | Powell, Hill, Surminski |
| Oct 15, 2024 | mjhl | Selkirk Steelers @ Winkler Flyers | 0–9 | 22 | Linesman | Peluk, Gramiak, Granger |
| Sep 20, 2024 | mjhl | Steinbach Pistons @ Winkler Flyers | 2–3 | 14 | Linesman | Wiebe, Burnell, Sibbald |
| Sep 13, 2024 | mjhl | Steinbach Pistons @ Winkler Flyers | 4–4 | 79 | Linesman | Letkeman, Wiebe, Sibbald |
| Mar 8, 2024 | mjhl | Portage Terriers @ Winkler Flyers | 2–1 | 46 | Linesman | Burnell, Swedlo, Granger |
| Feb 25, 2024 | mjhl | Selkirk Steelers @ Winkler Flyers | 3–5 | 108 | Linesman | Rapsky, Croker, Paul |
| Feb 23, 2024 | mjhl | Winnipeg Freeze @ Winkler Flyers | 1–2 | 16 | Linesman | Gramiak, Wiebe, Street |
| Feb 4, 2024 | mjhl | Swan Valley Stampeders @ Winkler Flyers | 0–7 | 8 | Linesman | Penner, Wilkinson, Letkeman |
| Jan 23, 2024 | mjhl | Winnipeg Blues @ Selkirk Steelers | 0–4 | 22 | Linesman | Zacharias, Wiebe, Street |
| Dec 10, 2023 | mjhl | Swan Valley Stampeders @ Winkler Flyers | 2–6 | 30 | Linesman | Powell, Wiebe, Matuszewski |
| Nov 17, 2023 | mjhl | Winnipeg Blues @ Winkler Flyers | 2–7 | 28 | Linesman | Mitchell, Cochrane, Matuszewski |
| Oct 29, 2023 | mjhl | Niverville Nighthawks @ Winkler Flyers | 1–3 | 56 | Linesman | Swedlo, Burnell, Street |
| Oct 24, 2023 | mjhl | Waywayseecappo Wolverines @ Portage Terriers | 3–6 | 24 | Linesman | Wiebe, Zacharias, Matuszewski |
| Oct 21, 2023 | mjhl | OCN Blizzard @ Winkler Flyers | 1–3 | 34 | Linesman | Wilkinson, Wither, Street |
| Sep 22, 2023 | mjhl | Winnipeg Blues @ Winkler Flyers | 1–3 | 12 | Linesman | Alward, Peluk, Granger |
| Mar 25, 2023 | mjhl | Steinbach Pistons @ Winkler Flyers | 3–2 | 28 | Linesman | Friesen, Swedlo, Miko |
| Mar 11, 2023 | mjhl | Neepawa Titans @ Winkler Flyers | 3–1 | 18 | Linesman | Comte, Scrivens |
| Mar 1, 2023 | mjhl | Selkirk Steelers @ Winkler Flyers | 1–2 | 28 | Linesman | Swedlo, Powell, Street |
