| Date | League | Matchup | Score | PIMs | Role | Officials |
|---|---|---|---|---|---|---|
| Nov 23, 2024 | mjhl | Steinbach Pistons @ Winkler Flyers | 1–3 | 54 | Linesman | Friesen, Wilkinson, Grenier |
| Nov 22, 2024 | mjhl | Swan Valley Stampeders @ Winkler Flyers | 4–3 | 18 | Linesman | Wood, Hill, Matuszewski |
| Oct 6, 2024 | mjhl | Portage Terriers @ Winkler Flyers | 1–4 | 36 | Linesman | Mitchell, Wiebe, |
| Mar 30, 2024 | mjhl | Portage Terriers @ Winkler Flyers | 3–6 | 8 | Linesman | Friesen, Wilkinson, Miko |
| Mar 27, 2024 | mjhl | Portage Terriers @ Winkler Flyers | 3–5 | 68 | Linesman | Comte, Powell, Cameron |
| Mar 13, 2024 | mjhl | Virden Oil Capitals @ Winkler Flyers | 4–2 | 47 | Linesman | Swedlo, Zacharias, Miko |
| Mar 10, 2024 | mjhl | Neepawa Titans @ Winkler Flyers | 3–5 | 46 | Linesman | Powell, Wood, Smith |
| Feb 23, 2024 | mjhl | Winnipeg Freeze @ Winkler Flyers | 1–2 | 16 | Linesman | Gramiak, Wiebe, Derksen |
| Jan 23, 2024 | mjhl | Winnipeg Blues @ Selkirk Steelers | 0–4 | 22 | Linesman | Zacharias, Wiebe, Derksen |
| Jan 19, 2024 | mjhl | Selkirk Steelers @ Winkler Flyers | 1–2 | 23 | Linesman | Wood, Mitchell, Fournier |
| Jan 17, 2024 | mjhl | Winnipeg Freeze @ Winkler Flyers | 4–6 | 34 | Linesman | Zacharias, Wither, Masi |
| Dec 20, 2023 | mjhl | Steinbach Pistons @ Winkler Flyers | 4–3 | 18 | Linesman | Peluk, Wood, Kile |
| Dec 16, 2023 | mjhl | Dauphin Kings @ Winkler Flyers | 4–7 | 34 | Linesman | Penner, Alward, Wiebe |
| Nov 22, 2023 | mjhl | Portage Terriers @ Winkler Flyers | 4–0 | 116 | Linesman | Zacharias, Wiebe, Smith |
| Oct 29, 2023 | mjhl | Niverville Nighthawks @ Winkler Flyers | 1–3 | 56 | Linesman | Swedlo, Burnell, Derksen |
| Oct 27, 2023 | mjhl | Winnipeg Freeze @ Niverville Nighthawks | 3–11 | 18 | Linesman | Wiebe, Wither, Matuszewski |
| Oct 21, 2023 | mjhl | OCN Blizzard @ Winkler Flyers | 1–3 | 34 | Linesman | Wilkinson, Wither, Derksen |
| Sep 24, 2023 | mjhl | Winnipeg Freeze @ Winkler Flyers | 1–5 | 36 | Linesman | Hofer, Wood, Fournier |
| Sep 13, 2023 | mjhl | Selkirk Steelers @ Winkler Flyers | 4–7 | 66 | Linesman | Zacharias, Hofer, Letkeman |
| Mar 15, 2023 | mjhl | Steinbach Pistons @ Winkler Flyers | 2–1 | 66 | Linesman | Peluk, Hofer, Wiebe |
| Mar 1, 2023 | mjhl | Selkirk Steelers @ Winkler Flyers | 1–2 | 28 | Linesman | Swedlo, Powell, Derksen |
| Feb 22, 2023 | mjhl | Winnipeg Freeze @ Winkler Flyers | 0–5 | 62 | Linesman | Zacharias, Swedlo, Derksen |
| Jan 20, 2023 | mjhl | Winnipeg Blues @ Winkler Flyers | 4–5 | 42 | Linesman | Wiebe, Derksen |
| Dec 18, 2022 | mjhl | Niverville Nighthawks @ Winkler Flyers | 2–5 | 34 | Linesman | Mitchell, Swedlo, Smith |
| Oct 21, 2022 | mjhl | OCN Blizzard @ Winkler Flyers | 4–3 | 34 | Linesman | Powell, Richardson, Derksen |
