| Oct 27, 2019 | mjhl | Virden Oil Capitals @ Winkler Flyers | 7–7 | 20 | Linesman | Hofer, Martens, Wall |
| Oct 15, 2019 | mjhl | Portage Terriers @ Winkler Flyers | 3–2 | 10 | Linesman | Wood, Wither, Cooke |
| Sep 28, 2019 | mjhl | OCN Blizzard @ Winkler Flyers | 4–6 | 44 | Linesman | Penner, Friesen |
| Sep 21, 2019 | mjhl | Steinbach Pistons @ Winkler Flyers | 3–1 | 22 | Linesman | Comte, Szczepanksi, Gauvin |
| Feb 16, 2019 | mjhl | Winnipeg Blues @ Winkler Flyers | 8–4 | 42 | Linesman | Penner, Hebert, Plett |
| Feb 12, 2019 | mjhl | Waywayseecappo Wolverines @ Winkler Flyers | 3–1 | 36 | Linesman | Peluk, Krieger, Gauvin |
| Feb 2, 2019 | mjhl | Steinbach Pistons @ Winkler Flyers | 5–0 | 32 | Linesman | Scrivens, Comte, Fitzsimmons |
| Feb 1, 2019 | mjhl | Neepawa Natives @ Winkler Flyers | 2–5 | 92 | Linesman | Hofer, Wood, Wolfe |
| Jan 26, 2019 | mjhl | Swan Valley Stampeders @ Winkler Flyers | 4–1 | 28 | Linesman | Penner, Kielich, Friesen |
| Jan 4, 2019 | mjhl | Dauphin Kings @ Winkler Flyers | 4–5 | 32 | Linesman | Powell, Mitchell, Zacharias |
| Dec 16, 2018 | mjhl | Portage Terriers @ Winkler Flyers | 5–4 | 54 | Linesman | Penner, Wolfe |
| Dec 4, 2018 | mjhl | Steinbach Pistons @ Winkler Flyers | 4–2 | 8 | Linesman | Krzyzaniak, Comte, Martens |
| Nov 27, 2018 | mjhl | Portage Terriers @ Winkler Flyers | 3–0 | 16 | Linesman | Peluk, Wolfe |
| Nov 20, 2018 | mjhl | Neepawa Natives @ Winkler Flyers | 5–1 | 48 | Linesman | Roeland, Dalgliesh, Martens |
| Nov 16, 2018 | mjhl | Dauphin Kings @ Winkler Flyers | 6–2 | 16 | Linesman | Penner, Hebert, Martens |
| Oct 21, 2018 | mjhl | Winnipeg Blues @ Winkler Flyers | 2–2 | 33 | Linesman | Comte, Krzyzaniak, Martens |
| Oct 19, 2018 | mjhl | OCN Blizzard @ Winkler Flyers | 0–1 | 28 | Linesman | Peluk, Wood, Martens |
| Oct 16, 2018 | mjhl | Virden Oil Capitals @ Winkler Flyers | 3–5 | 10 | Linesman | Roeland, Krieger, Martens |
| Oct 12, 2018 | mjhl | Waywayseecappo Wolverines @ Winkler Flyers | 4–1 | 34 | Linesman | Penner, Hebert, Bourgeois |
| Oct 5, 2018 | mjhl | Swan Valley Stampeders @ Winkler Flyers | 4–5 | 56 | Linesman | Hofer, Krieger, Martens |
| Oct 2, 2018 | mjhl | Selkirk Steelers @ Winkler Flyers | 4–1 | 48 | Linesman | MacDonald, Peluk, Gauvin |
| Sep 28, 2018 | mjhl | Steinbach Pistons @ Winkler Flyers | 6–2 | 46 | Linesman | MacDonald, Comte, Kile |
| Sep 21, 2018 | mjhl | Neepawa Natives @ Winkler Flyers | 3–4 | 60 | Linesman | Penner, Hebert, Martens |
| Mar 14, 2018 | mjhl | OCN Blizzard @ Winkler Flyers | 0–3 | 10 | Linesman | Penner, Dalgliesh, Gauvin |
| Feb 10, 2018 | mjhl | OCN Blizzard @ Winkler Flyers | 4–4 | 22 | Linesman | Scrivens, Comte, Surminski |
