| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 12/16 | 9:30 AM | Varsity | League | Normal | Away | New Canaan | | | | Wilton High School - Nicholas Zeoli Field House | 7:45 AM - 1 Bus - STA |
| Norwalk | | |
| Wilton | | |
| SAT 1/6 | 12:30 PM | Varsity | League | Normal | Away | Fairfield Ludlowe | | | | Wilton High School - Nicholas Zeoli Field House | 10:30 AM - 1 Bus - STA 1 bus |
| Fairfield Warde | | |
| Norwalk | | |
| Wilton | | |
| SAT 1/13 | 10:00 AM | Varsity | League | Normal | Away | Bridgeport Central | | | | Staples High School - Field House | 7:45 AM - 1 Bus - STA 1 bus |
| Darien | | |
| Greenwich | | |
| Stamford | | |
| Staples | | |
| St. Joseph | | |
| Westhill | | |
| SAT 1/20 | 9:30 AM | Varsity | League | Normal | Away | Bridgeport Central | | | | Wilton High School - Nicholas Zeoli Field House | 7:50 AM - 1 Bus - STA 1 bus |
| Brien McMahon | | |
| Greenwich | | |
| New Canaan | | |
| Stamford | | |
| St. Joseph | | |
| Wilton | | |
| SAT 1/27 | 10:00 AM | Varsity | Postseason | Normal | Away | Bridgeport Central | Loss | | | Staples High School - Field House | 7:50 AM - 1 Bus - STA 1 bus Boys |
| Brien McMahon | Loss | |
| Greenwich | Loss | 4-20 |
| Norwalk | Loss | |
| Staples | Loss | |
| Trumbull | Loss | |
| Westhill | Loss | |
| SAT 3/2 | 10:30 AM | Varsity | Postseason | Normal | Away | | | | | Reggie Lewis Center - The Track | 12:01 AM - Hertz Rental Van |