| 2023-24: 66th Annual Windsor Christmas Wrestling Tournament (Dec 28-29, 2023) |
| 2022-23: 65th Annual Windsor Christmas Wrestling Tournament (Dec 28-29, 2022) |
| 2021-22: 64th Annual Windsor Christmas Wrestling Tournament (Dec 29-30, 2021) |
| 2019-2020: 63rd Annual Windsor Christmas Wrestling Tournament (Dec 27-28, 2019) |
| 2018-19: 62nd Annual Windsor Christmas Wrestling Tournament (Dec 27-28, 2018) |
| 2017-18: 61st Annual Windsor Christmas Wrestling Tournament (Dec 28-29, 2017) |
| 2016-17: 60th Annual Windsor Christmas Wrestling Tournament (Dec 28-29, 2016) |
| 2015-16: 59th Annual Windsor Christmas Wrestling Tournament (Dec 28-29, 2015) |
| 2014-15: 58th Annual Windsor Christmas Wrestling Tournament (Dec 29-30, 2014) |
| 2013-14: 57th Annual Windsor Christmas Wrestling Tournament (Dec 27-28, 2013) |
| 2012-13: 56th Annual Windsor Christmas Wrestling Tournament (Dec 27-28, 2012) |
| 2011-12: 55th annual Windsor Christmas Wrestling Tournament (Dec 28-29, 2011) |
| 2010-11: 54th annual Windsor Christmas Wrestling Tournament (Dec 29-30, 2010) |
| 2009-2010: 53rd Annual Windsor Christmas Wrestling Tournament (Dec 28-29, 2009) |
| 2008-09: 52nd Annual Windsor Christmas Wrestling Tournament (Dec 27-28, 2008) |
| 1989-1990: 33rd Annual Windsor Christmas Wrestling Tournament (Dec 29-30, 1989) |
| 1988-89: 32nd Annual Windsor Christmas Wrestling Tournament (Dec 27-28, 1988) |
| 1980-81: 24th Annual Windsor Christmas Wrestling Tournament (Dec 29-30, 1980) |
| 1979-1980: 23rd Annual Windsor Christmas Wrestling Tournament (Dec 28-29, 1979) |
| 1975-76: 19th Annual Windsor Christmas Wrestling Tournament (Dec 29-30, 1975) |
| 1974-75: 18th Annual Windsor Christmas Wrestling Tournament (Dec 27-28, 1974) |
| 1973-74: 17th Annual Windsor Christmas Wrestling Tournament (Dec 27-28, 1973) |
| 1972-73: 16th Annual Windsor Christmas Wrestling Tournament (Dec 27-28, 1972) |
| 1971-72: 15th Annual Windsor Christmas Wrestling Tournament (Dec 28-29, 1971) |
| 1966-67: 10th Annual Windsor Christmas Wrestling Tournament (Dec 28-29, 1966) |
| 1965-66: 9th Annual Windsor Christmas Wrestling Tournament (Dec 28-29, 1965) |
| 1962-63: 6th Annual Windsor Christmas Wrestling Tournament (Dec 28-29, 1962) |
| 1961-62: 5th Annual Windsor Invitational Wrestling Tournament (Dec 29-30, 1961) |
| 1960-61: 4th Annual Windsor Christmas Wrestling Tournament (Dec 30, 1960) |
| 1959-1960: 3rd Annual Windsor Christmas Wrestling Tournament (Dec 29, 1959) |
| 1958-59: 2nd Annual Windsor Christmas Wrestling Tournament (Dec 27, 1958) |
| 1957-58: 1st Annual Windsor Christmas Wrestling Tournament (Dec 28, 1957) |
