| 2023-24: Hilton [NY] vs. Penfield [NY] (Dec 13, 2023) |
| 2020-21: Hilton [NY] vs. Penfield [NY] (Mar 6, 2021) |
| 2019-2020: Hilton [NY] vs. Penfield [NY] (Jan 15, 2020) |
| 2018-19: Hilton [NY] vs. Penfield [NY] (Jan 9, 2019) |
| 2017-18: Hilton [NY] vs. Penfield [NY] (Dec 20, 2017) |
| 2016-17: Hilton [NY] vs. Penfield [NY] (Dec 21, 2016) |
| 2016-17: Hilton [NY] vs. Penfield [NY] (Dec 21, 2016) |
| 2008-09: Hilton [NY] vs. Penfield [NY] (Jan 7, 2009) |
| 2002-03: Monroe County League Wrestling "East-West Day" (Feb 15, 2003) |
| 1979-1980: Hilton [NY] vs. Penfield [NY] (Feb 16, 1980) |
| 1967-68: Monroe County League Wrestling "East-West Day" (Feb 10, 1968) |
