| Feb 5, 2019 | mjhl | Selkirk Steelers @ Winkler Flyers | 5–6 | 10 | Linesman | Swedlo, Wood, Zacharias |
| Jan 25, 2019 | mjhl | Swan Valley Stampeders @ Winkler Flyers | 1–2 | 34 | Linesman | Dalgliesh, Powell, Smith |
| Dec 22, 2018 | mjhl | OCN Blizzard @ Winkler Flyers | 2–7 | 183 | Linesman | Krieger, MacDonald, Kile |
| Dec 21, 2018 | mjhl | OCN Blizzard @ Winkler Flyers | 5–6 | 61 | Linesman | Peluk, Wither, Smith |
| Dec 4, 2018 | mjhl | Steinbach Pistons @ Winkler Flyers | 4–2 | 8 | Linesman | Krzyzaniak, Comte, Derksen |
| Nov 20, 2018 | mjhl | Neepawa Natives @ Winkler Flyers | 5–1 | 48 | Linesman | Roeland, Dalgliesh, Derksen |
| Nov 17, 2018 | mjhl | Dauphin Kings @ Winkler Flyers | 5–6 | 182 | Linesman | Scrivens, Buffie, Wolfe |
| Nov 16, 2018 | mjhl | Dauphin Kings @ Winkler Flyers | 6–2 | 16 | Linesman | Penner, Hebert, Derksen |
| Oct 30, 2018 | mjhl | Winnipeg Blues @ Winkler Flyers | 3–4 | 48 | Linesman | Hofer, Roeland, Wolfe |
| Oct 21, 2018 | mjhl | Winnipeg Blues @ Winkler Flyers | 2–2 | 33 | Linesman | Comte, Krzyzaniak, Derksen |
| Oct 19, 2018 | mjhl | OCN Blizzard @ Winkler Flyers | 0–1 | 28 | Linesman | Peluk, Wood, Derksen |
| Oct 16, 2018 | mjhl | Virden Oil Capitals @ Winkler Flyers | 3–5 | 10 | Linesman | Roeland, Krieger, Derksen |
| Oct 5, 2018 | mjhl | Swan Valley Stampeders @ Winkler Flyers | 4–5 | 56 | Linesman | Hofer, Krieger, Derksen |
| Sep 21, 2018 | mjhl | Neepawa Natives @ Winkler Flyers | 3–4 | 60 | Linesman | Penner, Hebert, Derksen |
| Sep 15, 2018 | mjhl | Thief River Falls Norskies @ Winkler Flyers | 1–5 | 24 | Linesman | Hofer, Wolfe |
| Feb 21, 2018 | mjhl | Neepawa Natives @ Winkler Flyers | 3–6 | 56 | Referee | Penner, Zacharias, Plett |
| Jan 19, 2018 | mjhl | Virden Oil Capitals @ Winkler Flyers | 3–2 | 30 | Linesman | Hawthorn, Peluk, Stammers |
| Jan 13, 2018 | mjhl | Dauphin Kings @ Winkler Flyers | 1–4 | 101 | Linesman | Powell, Zacharias |
| Dec 5, 2017 | mjhl | Winnipeg Blues @ Winkler Flyers | 1–0 | 16 | Linesman | Mahoney, Dalgliesh, Zacharias |
| Nov 21, 2017 | mjhl | Portage Terriers @ Winkler Flyers | 6–3 | 10 | Linesman | Wood, Comte, Thiessen |
| Nov 17, 2017 | mjhl | Steinbach Pistons @ Winkler Flyers | 3–6 | 49 | Linesman | Dalgliesh, Kile |
| Nov 12, 2017 | mjhl | Neepawa Natives @ Winkler Flyers | 3–2 | 50 | Referee | Hawthorn, Wolfe, Granger |
| Oct 29, 2017 | mjhl | Selkirk Steelers @ Winkler Flyers | 1–7 | 18 | Linesman | Hawthorn, Derksen |
| Sep 6, 2016 | mjhl | Winnipeg Blues @ Winkler Flyers | 3–2 | 18 | Referee | Derksen |
| Nov 13, 2015 | mjhl | Dauphin Kings @ Winkler Flyers | 1–4 | 51 | Referee | — |
