| Wed 2/1 @ TBA | Varsity Basketball Game | vs. Hotchkiss (Lakeville, CT)* | | - |
| Wed 2/1 @ 2:30 PM | Varsity Girls Basketball Game | vs. Kent School (Kent, CT)* | | - |
| Wed 2/1 @ 2:30 PM | JV Basketball Game | vs. Hotchkiss (Lakeville, CT) | | - |
| Wed 2/1 @ 2:30 PM | JV Girls Basketball Game | vs. Kent School (Kent, CT) | | - |
| Wed 2/8 @ TBA | Varsity Basketball Game | vs. Deerfield Academy (Deerfield, MA) | | - |
| Wed 2/8 @ 2:30 PM | Varsity Girls Basketball Game | vs. Westminster (Simsbury, CT) | | - |
| Wed 2/8 @ 3:00 PM | Varsity Wrestling Game | vs. Hopkins (New Haven, CT) | | - |
| Fri 2/10 @ 4:30 PM | Varsity Basketball Game | vs. Salisbury School (Salisbury, CT) | | - |
| Fri 2/10 @ 5:00 PM | JV Basketball Game | vs. Salisbury School (Salisbury, CT) | | - |
| Sat 2/11 @ TBA | Varsity Basketball Game | vs. Avon Old Farms (Avon, CT)* | | - |
| Sat 2/11 @ 2:30 PM | Varsity Girls Basketball Game | vs. Hotchkiss (Lakeville, CT)* | | - |
| Sat 2/11 @ 4:00 PM | JV Girls Basketball Game | vs. Hotchkiss (Lakeville, CT) | | - |
| Sat 2/11 @ 5:30 PM | JV Basketball Game | vs. Avon (NY) | | - |
| Wed 2/15 @ 2:30 PM | JV Basketball Game | vs. Kent School (Kent, CT) | | - |
| Wed 2/15 @ 2:30 PM | Freshman Basketball Game | vs. Kent School (Kent, CT) | | - |
| Wed 2/15 @ 2:30 PM | Varsity Basketball Game | vs. Kent School (Kent, CT)* | | - |
| Sat 2/18 @ 2:30 PM | Freshman Basketball Game | vs. Berkshire Country Day (Lenox, MA) | | - |
| Sat 2/18 @ 4:00 PM | Varsity Basketball Game | vs. Loomis Chaffee (Windsor, CT) | | - |
| Tue 2/21 @ 4:30 PM | Varsity Girls Basketball Game | vs. Miss Porter's (Farmington, CT) | | - |
| Wed 2/22 @ 2:30 PM | Freshman Basketball Game | vs. Avon (NY) | | - |
| Wed 2/22 @ 2:30 PM | Varsity Girls Basketball Game | vs. Berkshire School (Sheffield, MA)* | | - |
| Wed 2/22 @ 2:30 PM | Varsity Girls Basketball Game | vs. Berkshire Country Day (Lenox, MA) | | - |
| Wed 2/22 @ 4:00 PM | Varsity Basketball Game | vs. Avon Old Farms (Avon, CT)* | | - |
| Wed 2/22 @ 4:00 PM | JV Girls Basketball Game | vs. Berkshire Country Day (Lenox, MA) | | - |
| Sat 2/25 @ 3:00 PM | Varsity Girls Basketball Game | vs. Hotchkiss (Lakeville, CT)* | | - |
| Sat 2/25 @ 3:00 PM | JV Girls Basketball Game | vs. Hotchkiss (Lakeville, CT) | | - |
| Sat 2/25 @ 4:00 PM | Varsity Basketball Game | vs. Westminster (Simsbury, CT) | | - |