| Feb 22, 2023 | mjhl | Winnipeg Freeze @ Winkler Flyers | 0–5 | 62 | Linesman | Zacharias, Swedlo, Street |
| Feb 3, 2023 | mjhl | Winnipeg Blues @ Winkler Flyers | 1–4 | 18 | Linesman | Zacharias, Gramiak, Wiebe |
| Jan 27, 2023 | mjhl | Neepawa Titans @ Winkler Flyers | 2–4 | 18 | Linesman | Wilkinson, Penner, Wiebe |
| Jan 20, 2023 | mjhl | Winnipeg Blues @ Winkler Flyers | 4–5 | 42 | Referee | Wiebe, Street |
| Jan 18, 2023 | mjhl | Portage Terriers @ Winkler Flyers | 4–3 | 56 | Linesman | Peluk, Powell, Wiebe |
| Jan 13, 2023 | mjhl | Niverville Nighthawks @ Winkler Flyers | 4–2 | 44 | Linesman | Croker, Croker |
| Dec 21, 2022 | mjhl | Portage Terriers @ Winkler Flyers | 3–1 | 54 | Linesman | Penner, Friesen, Wiebe |
| Dec 9, 2022 | mjhl | Portage Terriers @ Winkler Flyers | 5–8 | 38 | Linesman | Scrivens, Gagnon, Grenier |
| Dec 2, 2022 | mjhl | Dauphin Kings @ Winkler Flyers | 1–3 | 79 | Linesman | Gramiak, Comte, Wiebe |
| Nov 2, 2022 | mjhl | Steinbach Pistons @ Winkler Flyers | 4–1 | 12 | Linesman | Penner, Wiebe |
| Oct 22, 2022 | mjhl | Swan Valley Stampeders @ Winkler Flyers | 1–3 | 24 | Linesman | Penner, Wiebe |
| Oct 21, 2022 | mjhl | OCN Blizzard @ Winkler Flyers | 4–3 | 34 | Linesman | Powell, Richardson, Street |
| Oct 12, 2022 | mjhl | Virden Oil Capitals @ Winkler Flyers | 4–5 | 50 | Linesman | Wiebe, Mitchell, Smith |
| Oct 2, 2022 | mjhl | Waywayseecappo Wolverines @ Winkler Flyers | 2–1 | 20 | Linesman | Martens, Wiebe, Granger |
| Sep 24, 2022 | mjhl | OCN Blizzard @ Winkler Flyers | 1–3 | 26 | Linesman | Wood, Comte, Hill |
| Sep 21, 2022 | mjhl | Niverville Nighthawks @ Winkler Flyers | 5–1 | 78 | Linesman | Hofer, MacDonald |
| Sep 17, 2022 | mjhl | Winnipeg Blues @ Winkler Flyers | 2–7 | 28 | Linesman | Friesen, Wilkinson, Hill |
| Sep 9, 2022 | mjhl | Steinbach Pistons @ Winkler Flyers | 0–6 | 32 | Linesman | Wiebe, Martens, Wolfe |
| Apr 21, 2022 | mjhl | Dauphin Kings @ Winkler Flyers | 5–2 | 40 | Linesman | MacDonald, Comte, Buffie |
| Apr 3, 2022 | mjhl | Winnipeg Blues @ Winkler Flyers | 1–3 | 22 | Linesman | Penner, Friesen, Wiebe |
| Mar 25, 2022 | mjhl | Winnipeg Blues @ Winkler Flyers | 3–9 | 30 | Linesman | Powell, Peluk, Cooke |
| Mar 12, 2022 | mjhl | Portage Terriers @ Winkler Flyers | 1–7 | 145 | Linesman | Ginter, Scrivens, Kile |
| Mar 2, 2022 | mjhl | Selkirk Steelers @ Winkler Flyers | 4–4 | 48 | Linesman | Ginter, Hofer, Wiebe |
| Feb 25, 2022 | mjhl | Portage Terriers @ Winkler Flyers | 2–6 | 20 | Linesman | Richardson, Szczepanksi, Street |
| Feb 23, 2022 | mjhl | Selkirk Steelers @ Winkler Flyers | 2–1 | 12 | Linesman | Kielich, Friesen, Wiebe |
