| Apr 1, 2022 | mjhl | Winnipeg Blues @ Winkler Flyers | 3–4 | 32 | Referee | MacDonald, Lyle, Cooke |
| Mar 12, 2022 | mjhl | Portage Terriers @ Winkler Flyers | 1–7 | 145 | Referee | Scrivens, Kile, Derksen |
| Mar 2, 2022 | mjhl | Selkirk Steelers @ Winkler Flyers | 4–4 | 48 | Referee | Hofer, Wiebe, Derksen |
| Jan 9, 2022 | mjhl | Dauphin Kings @ Winkler Flyers | 3–4 | 20 | Referee | Penner, Wiebe, Derksen |
| Dec 18, 2021 | mjhl | OCN Blizzard @ Winkler Flyers | 1–4 | 40 | Referee | Penner, Hill, Wiebe |
| Dec 17, 2021 | mjhl | OCN Blizzard @ Winkler Flyers | 6–8 | 80 | Referee | Mitchell, Derksen, Street |
| Dec 5, 2021 | mjhl | Virden Oil Capitals @ Winkler Flyers | 3–1 | 54 | Referee | Wilkinson, Wiebe, Street |
| Nov 19, 2021 | mjhl | Waywayseecappo Wolverines @ Neepawa Titans | 5–3 | 84 | Referee | Swedlo, Martens, Cameron |
| Oct 8, 2021 | mjhl | Steinbach Pistons @ Winkler Flyers | 2–3 | 12 | Referee | Martens, Wiebe |
| Sep 18, 2021 | mjhl | Portage Terriers @ Winkler Flyers | 4–6 | 138 | Referee | Martens, Street, Wiebe |
| Sep 8, 2021 | mjhl | Selkirk Steelers @ Winkler Flyers | 5–2 | 26 | Referee | Martens, Derksen, Street |
| Sep 4, 2021 | mjhl | Steinbach Pistons @ Winkler Flyers | 3–4 | 14 | Referee | Wither, Wiebe |
| Oct 24, 2020 | mjhl | Virden Oil Capitals @ Winkler Flyers | 5–2 | 31 | Referee | Friesen, Derksen, Martens |
| Oct 10, 2020 | mjhl | Neepawa Titans @ Winkler Flyers | 1–4 | 20 | Referee | Martens, Wiebe, Derksen |
| Sep 23, 2020 | mjhl | Selkirk Steelers @ Winkler Flyers | 3–3 | 54 | Referee | Martens |
| Oct 21, 2016 | mjhl | OCN Blizzard @ Winkler Flyers | 1–5 | 34 | Referee | — |
| Sep 27, 2016 | mjhl | Virden Oil Capitals @ Winkler Flyers | 3–2 | 18 | Referee | Beattie, Zacharias |
| Oct 9, 2015 | mjhl | Winnipeg Blues @ Winkler Flyers | 2–3 | 18 | Referee | Martens, Bergstresser |
| Feb 21, 2015 | mjhl | Virden Oil Capitals @ Winkler Flyers | 1–5 | 32 | Referee | Bergstresser, Martens |
| Jan 4, 2015 | mjhl | Waywayseecappo Wolverines @ Steinbach Pistons | 0–3 | 18 | Referee | Hawthorn |
| Oct 10, 2014 | mjhl | OCN Blizzard @ Winkler Flyers | 0–0 | 20 | Referee | — |
| Sep 19, 2014 | mjhl | Steinbach Pistons @ Winkler Flyers | 2–4 | 12 | Referee | Martens |
