| Jan 19, 2022 | mjhl | Winnipeg Freeze @ Winkler Flyers | 2–7 | 72 | Linesman | Peluk, Hinds, McConnell |
| Jan 9, 2022 | mjhl | Dauphin Kings @ Winkler Flyers | 3–4 | 20 | Linesman | Penner, Ginter, Wiebe |
| Dec 17, 2021 | mjhl | OCN Blizzard @ Winkler Flyers | 6–8 | 80 | Linesman | Ginter, Mitchell, Street |
| Dec 12, 2021 | mjhl | Neepawa Titans @ Winkler Flyers | 4–6 | 88 | Linesman | Peluk, Hinds, Wiebe |
| Nov 22, 2021 | mjhl | Selkirk Steelers @ Virden Oil Capitals | 4–6 | 14 | Linesman | Szczepanksi, Wither, Hill |
| Nov 17, 2021 | mjhl | Selkirk Steelers @ Winkler Flyers | 3–3 | 26 | Linesman | Kielich, Penner, Martens |
| Nov 5, 2021 | mjhl | Winnipeg Blues @ Winkler Flyers | 1–4 | 16 | Linesman | MacDonald, Scrivens, Martens |
| Oct 30, 2021 | mjhl | Winnipeg Blues @ Winkler Flyers | 4–3 | 28 | Linesman | Hofer, MacDonald, McConnell |
| Oct 2, 2021 | mjhl | Steinbach Pistons @ Winkler Flyers | 4–1 | 8 | Linesman | Wither, Szczepanksi, Street |
| Sep 24, 2021 | mjhl | Portage Terriers @ Winkler Flyers | 3–4 | 86 | Linesman | Peluk, Alward, Hill |
| Sep 11, 2021 | mjhl | Virden Oil Capitals @ Winkler Flyers | 4–4 | 14 | Linesman | Burnell, Wither, Martens |
| Sep 8, 2021 | mjhl | Selkirk Steelers @ Winkler Flyers | 5–2 | 26 | Linesman | Ginter, Martens, Street |
| Oct 24, 2020 | mjhl | Virden Oil Capitals @ Winkler Flyers | 5–2 | 31 | Linesman | Friesen, Ginter, Martens |
| Oct 10, 2020 | mjhl | Neepawa Titans @ Winkler Flyers | 1–4 | 20 | Linesman | Ginter, Martens, Wiebe |
| Mar 6, 2020 | mjhl | Virden Oil Capitals @ Winkler Flyers | 1–0 | 42 | Linesman | Hawthorn, Friesen, Buffie |
| Feb 22, 2020 | mjhl | Waywayseecappo Wolverines @ Winkler Flyers | 1–5 | 84 | Linesman | Penner, Friesen, Wall |
| Feb 7, 2020 | mjhl | Neepawa Natives @ Winkler Flyers | 3–5 | 35 | Linesman | Swedlo, Szczepanksi, Wall |
| Feb 1, 2020 | mjhl | Swan Valley Stampeders @ Winkler Flyers | 2–3 | 16 | Linesman | Penner, Friesen, Wall |
| Jan 26, 2020 | mjhl | Virden Oil Capitals @ Winkler Flyers | 5–3 | 46 | Linesman | Penner, Friesen, Wall |
| Jan 7, 2020 | mjhl | Winnipeg Blues @ Winkler Flyers | 4–6 | 12 | Linesman | Wither, Friesen, Wall |
| Dec 22, 2019 | mjhl | Winnipeg Blues @ Winkler Flyers | 2–4 | 25 | Linesman | Szczepanski, Mitchell, Wall |
| Dec 20, 2019 | mjhl | Steinbach Pistons @ Winkler Flyers | 1–1 | 18 | Linesman | Hawthorn, Swedlo, Wall |
| Dec 13, 2019 | mjhl | Dauphin Kings @ Winkler Flyers | 2–5 | 12 | Linesman | Burnell, Comte, Wall |
| Nov 19, 2019 | mjhl | Selkirk Steelers @ Winkler Flyers | 4–7 | 45 | Linesman | Richardson, Kielich, Wolfe |
| Nov 16, 2019 | mjhl | Swan Valley Stampeders @ Winkler Flyers | 4–5 | 20 | Linesman | Penner, Kielich |
