| Wed 2/1 @ TBA | Varsity Girls Basketball Game | vs. Worcester Academy (Worcester, MA) | | - |
| Wed 2/1 @ 2:30 PM | Varsity Basketball Game | vs. Loomis Chaffee (Windsor, CT) | | - |
| Wed 2/8 @ 3:00 PM | Varsity Girls Basketball Game | vs. Deerfield Academy (Deerfield, MA) | | - |
| Wed 2/8 @ 3:30 PM | Varsity Basketball Game | vs. Cheshire Academy (Cheshire, CT)* | | - |
| Wed 2/8 @ 6:00 PM | Varsity Wrestling Game | vs. Canton (CT) | | - |
| Fri 2/10 @ 6:15 PM | Varsity Girls Basketball Game | vs. Phillips Academy (Andover, MA) | | - |
| Wed 2/15 @ 2:30 PM | Varsity Girls Basketball Game | vs. Loomis Chaffee (Windsor, CT) | | - |
| Wed 2/15 @ 3:00 PM | Varsity Basketball Game | vs. Deerfield Academy (Deerfield, MA) | | - |
| Fri 2/17 @ 4:30 PM | Varsity Girls Basketball Game | vs. Miss Porter's (Farmington, CT) | | - |
| Sat 2/18 @ 4:00 PM | Varsity Girls Basketball Game | vs. Westminster (Simsbury, CT)* | | - |
| Sat 2/18 @ 7:30 PM | Varsity Basketball Game | vs. Williston Northampton (Easthampton, MA)* | | - |
| Wed 2/22 @ 4:00 PM | Varsity Basketball Game | vs. Gunnery (Washington, CT)* | | - |
| Sat 2/25 @ 7:00 PM | Varsity Basketball Game | vs. Salisbury School (Salisbury, CT) | | - |
| Wed 2/29 @ TBA | Varsity Basketball Game | vs. TBA*** | | - |