| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 12/16 | 12:30 PM | Varsity | League | Normal | Away | Fairfield Warde | | | | Wilton High School - Nicholas Zeoli Field House | 11:00 AM - 1 Bus - Share with Girls Track |
| Brien McMahon | | |
| Darien | | |
| Wilton | | |
| SAT 1/6 | 9:30 AM | Varsity | League | Normal | Away | New Canaan | | | | Wilton High School - Nicholas Zeoli Field House | 8:00 AM - 1 Bus |
| Wilton | | |
| Darien | | |
| SAT 1/13 | 9:30 AM | Varsity | League | Normal | Away | Trumbull | | | | Wilton High School - Nicholas Zeoli Field House | 8:00 AM - 2 Buses |
| Norwalk | | |
| Wilton | | |
| New Canaan | | |
| Brien McMahon | | |
| Fairfield Warde | | |
| Fairfield Ludlowe | | |
| SAT 1/20 | 10:00 AM | Varsity | League | Normal | Away | Trumbull | | | | Staples High School - Field House | 8:15 AM - 1 Bus |
| Darien | | |
| Norwalk | | |
| Staples | | |
| Fairfield Ludlowe | | |
| Westhill | | |
| Fairfield Warde | | |
| SAT 3/2 | 12:01 AM | Varsity | Postseason | Normal | Away | | | | | TBA - TBA | |