| Sep 11, 2022 | mjhl | Selkirk Steelers @ Winkler Flyers | 2–1 | 66 | Linesman | Martens, Wiebe, Hill |
| Sep 9, 2022 | mjhl | Steinbach Pistons @ Winkler Flyers | 0–6 | 32 | Linesman | Wiebe, Martens, Derksen |
| Jan 29, 2022 | mjhl | Swan Valley Stampeders @ Neepawa Titans | 5–1 | 80 | Linesman | Alward, Wiebe, McConnell |
| Oct 15, 2021 | mjhl | Winnipeg Freeze @ Winkler Flyers | 5–8 | 26 | Linesman | Kielich, Penner, Street |
| Oct 30, 2020 | mjhl | Virden Oil Capitals @ Winkler Flyers | 5–3 | 22 | Linesman | Penner, Wilkinson, Wall |
| Dec 14, 2019 | mjhl | Dauphin Kings @ Winkler Flyers | 2–8 | 76 | Linesman | Penner, Friesen, Wall |
| Nov 19, 2019 | mjhl | Selkirk Steelers @ Winkler Flyers | 4–7 | 45 | Linesman | Richardson, Kielich, Derksen |
| Oct 26, 2019 | mjhl | Neepawa Natives @ Winkler Flyers | 5–6 | 14 | Linesman | Peluk, MacDonald, Cooke |
| Sep 13, 2019 | mjhl | Steinbach Pistons @ Winkler Flyers | 6–4 | 114 | Linesman | Krzyzaniak, Martens |
| Sep 4, 2019 | mjhl | Virden Oil Capitals @ Winkler Flyers | 9–2 | 18 | Referee | Martens |
| Feb 8, 2019 | mjhl | Selkirk Steelers @ Neepawa Natives | 4–3 | 98 | Linesman | Beck, Drysdale |
| Feb 1, 2019 | mjhl | Neepawa Natives @ Winkler Flyers | 2–5 | 92 | Linesman | Hofer, Wood, Derksen |
| Dec 16, 2018 | mjhl | Portage Terriers @ Winkler Flyers | 5–4 | 54 | Linesman | Penner, Derksen |
| Nov 27, 2018 | mjhl | Portage Terriers @ Winkler Flyers | 3–0 | 16 | Linesman | Peluk, Derksen |
| Nov 17, 2018 | mjhl | Dauphin Kings @ Winkler Flyers | 5–6 | 182 | Linesman | Scrivens, Buffie, Martens |
| Nov 9, 2018 | mjhl | Waywayseecappo Wolverines @ Winkler Flyers | 4–1 | 164 | Linesman | Mitchell, Comte, Smith |
| Oct 30, 2018 | mjhl | Winnipeg Blues @ Winkler Flyers | 3–4 | 48 | Linesman | Hofer, Roeland, Martens |
| Sep 15, 2018 | mjhl | Thief River Falls Norskies @ Winkler Flyers | 1–5 | 24 | Linesman | Hofer, Martens |
| Sep 4, 2018 | mjhl | Neepawa Natives @ Winkler Flyers | 0–3 | 6 | Linesman | Wood, Granger |
| Nov 12, 2017 | mjhl | Neepawa Natives @ Winkler Flyers | 3–2 | 50 | Linesman | Hawthorn, Martens, Granger |
