| 02/15/2026 01:30 AM UTC |  Winkler Flyers |  Waywayseecappo Wolverines | - | MJHL |
| 11/19/2025 01:30 AM UTC | Waywayseecappo Wolverines | Winkler Flyers | 3 - 5 | MJHL |
| 11/15/2025 01:30 AM UTC | Winkler Flyers | Waywayseecappo Wolverines | 5 - 0 | MJHL |
| 09/26/2025 12:30 AM UTC | Waywayseecappo Wolverines | Winkler Flyers | 3 - 8 | MJHL |
| 03/03/2025 01:30 AM UTC | Winkler Flyers | Waywayseecappo Wolverines | 4 - 1 | MJHL |
| 02/16/2025 01:30 AM UTC | Winkler Flyers | Waywayseecappo Wolverines | 6 - 2 | MJHL |
| 01/15/2025 01:30 AM UTC | Waywayseecappo Wolverines | Winkler Flyers | 4 - 7 | MJHL |
| 11/27/2024 01:30 AM UTC | Waywayseecappo Wolverines | Winkler Flyers | 1 - 2 | MJHL |
| 01/28/2024 09:00 PM UTC | Winkler Flyers | Waywayseecappo Wolverines | 5 - 2 | MJHL |
| 01/22/2024 12:00 AM UTC | Waywayseecappo Wolverines | Winkler Flyers | 3 - 4 | MJHL |
| 12/07/2023 01:30 AM UTC | Waywayseecappo Wolverines | Winkler Flyers | 2 - 5 | MJHL |
| 10/15/2023 08:00 PM UTC | Winkler Flyers | Waywayseecappo Wolverines | 9 - 0 | MJHL |
| 11/20/2022 01:30 AM UTC | Waywayseecappo Wolverines | Winkler Flyers | 1 - 4 | MJHL |
| 11/19/2022 01:00 AM UTC | Winkler Flyers | Waywayseecappo Wolverines | 4 - 1 | MJHL |
| 10/02/2022 08:00 PM UTC | Winkler Flyers | Waywayseecappo Wolverines | 1 - 2 | MJHL |
| 09/30/2022 11:00 PM UTC | Waywayseecappo Wolverines | Winkler Flyers | 3 - 2 | MJHL |
| 01/16/2022 09:00 PM UTC | Winkler Flyers | Waywayseecappo Wolverines | 2 - 3 | MJHL |
| 01/15/2022 01:30 AM UTC | Waywayseecappo Wolverines | Winkler Flyers | 4 - 1 | MJHL |
| 01/24/2021 01:00 AM UTC | Waywayseecappo Wolverines | Winkler Flyers | PPD | MJHL |
| 01/23/2021 01:30 AM UTC | Winkler Flyers | Waywayseecappo Wolverines | PPD | MJHL |