| Tue, Sep 14
| 4:00 p.m. | Westhill, Greenwich, Ridge | Scofield Magnet MS- | | | |
| Westhill, Greenwich, Ridge | Scofield Magnet MS- |
| Tue, Sep 21
| 4:00 p.m. | Wilton, New Canaan, Staple | Allen's Meadow- XC C | | | |
| Wilton, New Canaan, Staple | Allen's Meadow- XC C |
| Tue, Sep 28
| 4:00 p.m. | Fairfield Warde, Norwalk, | Fairfield Warde HS- | | | |
| Fairfield Warde, Norwalk, | Fairfield Warde HS- |
| Tue, Oct 05
| 4:00 p.m. | Danbury, Brian McMahon | Tarrywile Park | | | |
| Danbury, Brian McMahon | Tarrywile Park |
| Tue, Oct 12
| 4:00 p.m. | Fairfield Ludlowe, Darien, | Fairfield Ludlowe HS | | | |
| Fairfield Ludlowe, Darien, | Fairfield Ludlowe HS |
| Sat, Oct 30
| 1:30 p.m. | CIAC Cross Country Class L | Wickham Park | | | |
| CIAC Cross Country Class L | Wickham Park |
| Fri, Nov 05
| 2:45 p.m. | CIAC Cross Country Open Ch | Wickham Park | | | |
| CIAC Cross Country Open Ch | Wickham Park |
