| Oct 2, 2022 | mjhl | Waywayseecappo Wolverines @ Winkler Flyers | 2–1 | 20 | Referee | Wiebe, Granger, Derksen |
| Sep 11, 2022 | mjhl | Selkirk Steelers @ Winkler Flyers | 2–1 | 66 | Referee | Wiebe, Wolfe, Hill |
| Sep 9, 2022 | mjhl | Steinbach Pistons @ Winkler Flyers | 0–6 | 32 | Referee | Wiebe, Derksen, Wolfe |
| Nov 19, 2021 | mjhl | Waywayseecappo Wolverines @ Neepawa Titans | 5–3 | 84 | Linesman | Swedlo, Ginter, Cameron |
| Nov 17, 2021 | mjhl | Selkirk Steelers @ Winkler Flyers | 3–3 | 26 | Linesman | Kielich, Penner, Derksen |
| Nov 5, 2021 | mjhl | Winnipeg Blues @ Winkler Flyers | 1–4 | 16 | Linesman | MacDonald, Scrivens, Derksen |
| Oct 8, 2021 | mjhl | Steinbach Pistons @ Winkler Flyers | 2–3 | 12 | Referee | Ginter, Wiebe |
| Sep 18, 2021 | mjhl | Portage Terriers @ Winkler Flyers | 4–6 | 138 | Referee | Ginter, Street, Wiebe |
| Sep 11, 2021 | mjhl | Virden Oil Capitals @ Winkler Flyers | 4–4 | 14 | Linesman | Burnell, Wither, Derksen |
| Sep 8, 2021 | mjhl | Selkirk Steelers @ Winkler Flyers | 5–2 | 26 | Referee | Ginter, Derksen, Street |
| Oct 24, 2020 | mjhl | Virden Oil Capitals @ Winkler Flyers | 5–2 | 31 | Linesman | Friesen, Ginter, Derksen |
| Oct 10, 2020 | mjhl | Neepawa Titans @ Winkler Flyers | 1–4 | 20 | Referee | Ginter, Wiebe, Derksen |
| Sep 23, 2020 | mjhl | Selkirk Steelers @ Winkler Flyers | 3–3 | 54 | Linesman | Ginter |
| Mar 10, 2020 | mjhl | Virden Oil Capitals @ Winkler Flyers | 7–1 | 98 | Linesman | Scrivens, Kielich, Gramiak |
| Feb 18, 2020 | mjhl | Selkirk Steelers @ Winkler Flyers | 0–1 | 32 | Linesman | Peluk, Benroth, Wall |
| Feb 2, 2020 | mjhl | OCN Blizzard @ Winkler Flyers | 3–4 | 42 | Linesman | Szczepanksi, Hawthorn, Wall |
| Jan 28, 2020 | mjhl | Neepawa Natives @ Winkler Flyers | 2–4 | 20 | Linesman | Penner, Kielich, Wall |
| Jan 27, 2020 | mjhl | Portage Terriers @ Winkler Flyers | 1–3 | 16 | Linesman | Peluk, Powell, Buffie |
| Jan 14, 2020 | mjhl | Steinbach Pistons @ Winkler Flyers | 2–3 | 22 | Linesman | Dalgliesh, Scrivens, Ryden |
| Nov 15, 2019 | mjhl | Swan Valley Stampeders @ Winkler Flyers | 2–2 | 43 | Linesman | Peluk, Burnell, Wall |
| Oct 27, 2019 | mjhl | Virden Oil Capitals @ Winkler Flyers | 7–7 | 20 | Referee | Hofer, Wall, Derksen |
| Sep 13, 2019 | mjhl | Steinbach Pistons @ Winkler Flyers | 6–4 | 114 | Linesman | Krzyzaniak, Wolfe |
| Sep 4, 2019 | mjhl | Virden Oil Capitals @ Winkler Flyers | 9–2 | 18 | Referee | Wolfe |
| Feb 24, 2019 | mjhl | Portage Terriers @ Winkler Flyers | 5–1 | 61 | Linesman | Dalgliesh, Comte, Scrivens |
| Feb 15, 2019 | mjhl | Selkirk Steelers @ Winkler Flyers | 3–1 | 24 | Linesman | MacDonald, Comte, Prokop |
