| Year | Sport | Class | Champion | Runner-up | Score | Details |
| 2011 | Football | S | Holy Cross | Cromwell | 34-27 |  |
| 2006 | Football | SS | Holy Cross | Stratford | 40-0 | |
| 2004 | Football | SS | Woodland | Holy Cross | 35-0 | |
| 1996 | Football | L | Weaver | Holy Cross | 47-8 | |
| 1984 | Football | L-II | Wilbur Cross | Holy Cross | 3-0 |