| Wed 2/1 @ 3:00 PM | Varsity Basketball Game | vs. Kent School (Kent, CT)* | | - |
| Wed 2/1 @ 3:00 PM | Varsity Wrestling Game | vs. Choate Rosemary Hall (Wallingford, CT) | | - |
| Wed 2/8 @ 3:00 PM | Varsity Basketball Game | vs. Kent School (Kent, CT)* | | - |
| Wed 2/8 @ 3:00 PM | Varsity Wrestling Game | vs. Canterbury (New Milford, CT)* | | - |
| Fri 2/10 @ 7:00 PM | Varsity Basketball Game | vs. Choate Rosemary Hall (Wallingford, CT) | | - |
| Sat 2/11 @ TBA | Varsity Basketball Game | vs. Taft (Watertown, CT)* | | - |
| Wed 2/15 @ 3:00 PM | Varsity Basketball Game | vs. Hotchkiss (Lakeville, CT)* | | - |
| Sat 2/18 @ 7:00 PM | Varsity Basketball Game | vs. Berkshire School (Sheffield, MA) | | - |
| Wed 2/22 @ 4:00 PM | Varsity Basketball Game | vs. Taft (Watertown, CT)* | | - |
| Fri 2/24 @ 4:00 PM | Varsity Basketball Game | vs. Williston Northampton (Easthampton, MA) | | - |
| Sat 2/25 @ 7:30 PM | Varsity Basketball Game | vs. Canterbury (New Milford, CT)* | | - |