| 2025-26: Churchville-Chili [NY] vs. Irondequoit [NY] (Jan 28, 2026) |
| 2024-25: Churchville-Chili [NY] vs. Irondequoit [NY] (Jan 15, 2025) |
| 2023-24: 42nd Annual DeMeco-Trainor Memorial Wrestling Tournament (Dec 9, 2023) |
| 2023-24: Churchville-Chili [NY] vs. Irondequoit [NY] (Nov 29, 2023) |
| 2022-23: 41st Annual DeMeco-Trainor Memorial Wrestling Tournament (Dec 10, 2022) |
| 2021-22: Churchville-Chili [NY] vs. Irondequoit [NY] (Jan 5, 2022) |
| 2021-22: 40th Annual DeMeco-Trainor Memorial Wrestling Tournament (Dec 11, 2021) |
| 2018-19: 37th Annual DeMeco-Trainor Memorial Wrestling Tournament (Dec 8, 2018) |
| 2017-18: 36th Annual DeMeco-Trainor Memorial Wrestling Tournament (Dec 9, 2017) |
| 2016-17: 35th Annual DeMeco-Trainor Memorial Wrestling Tournament (Dec 10, 2016) |
| 2014-15: 33rd Annual DeMeco-Trainor Memorial Wrestling Tournament (Dec 13, 2014) |
| 2012-13: 31st Annual DeMeco-Trainor Memorial Wrestling Tournament (Dec 15, 2012) |
| 2009-2010: Churchville-Chili [NY] vs. Irondequoit [NY] (Jan 6, 2010) |
| 2008-09: Churchville-Chili [NY] vs. Irondequoit [NY] (Jan 14, 2009) |
| 2006-07: Churchville-Chili [NY] vs. Irondequoit [NY] (Jan 10, 2007) |
| 1984-85: Monroe County League "East-West Day" (Feb 9, 1985) |
| 1977-78: Churchville-Chili [NY] vs. Irondequoit [NY] (Feb 18, 1978) |
| 1971-72: Churchville-Chili [NY] vs. Irondequoit [NY] (Jan 8, 1972) |
| 1968-69: Churchville-Chili [NY] vs. Irondequoit [NY] (Jan 25, 1969) |
