| Wed 2/1 @ TBA | Varsity Basketball Game | vs. Taft (Watertown, CT)* | | - |
| Wed 2/1 @ 2:00 PM | Varsity Girls Basketball Game | vs. Berkshire School (Sheffield, MA)* | | - |
| Wed 2/1 @ 2:30 PM | JV Basketball Game | vs. Taft (Watertown, CT) | | - |
| Wed 2/8 @ 2:30 PM | Freshman Basketball Game | vs. Canterbury (New Milford, CT) | | - |
| Wed 2/8 @ 2:30 PM | JV Girls Basketball Game | vs. Kent School (Kent, CT) | | - |
| Wed 2/8 @ 2:30 PM | Varsity Girls Basketball Game | vs. Kent School (Kent, CT)* | | - |
| Wed 2/8 @ 4:30 PM | Varsity Basketball Game | vs. Canterbury (New Milford, CT)* | | - |
| Wed 2/8 @ 4:30 PM | JV Basketball Game | vs. Canterbury (New Milford, CT) | | - |
| Fri 2/10 @ 4:30 PM | Varsity Basketball Game | vs. Berkshire Country Day (Lenox, MA) | | - |
| Fri 2/10 @ 4:30 PM | Varsity Basketball Game | vs. Berkshire School (Sheffield, MA) | | - |
| Sat 2/11 @ 2:30 PM | Varsity Girls Basketball Game | vs. Taft (Watertown, CT)* | | - |
| Sat 2/11 @ 2:30 PM | JV Basketball Game | vs. Trinity-Pawling (Pawling, NY) | | - |
| Sat 2/11 @ 2:30 PM | Freshman Basketball Game | vs. Kent School (Kent, CT) | | - |
| Sat 2/11 @ 4:00 PM | JV Girls Basketball Game | vs. Taft (Watertown, CT) | | - |
| Wed 2/15 @ 1:30 PM | Freshman Basketball Game | vs. Salisbury School (Salisbury, CT) | | - |
| Wed 2/15 @ 3:00 PM | Varsity Basketball Game | vs. Avon Old Farms (Avon, CT)* | | - |
| Wed 2/15 @ 3:00 PM | JV Basketball Game | vs. Avon (NY) | | - |
| Wed 2/15 @ 4:30 PM | Varsity Girls Basketball Game | vs. Choate Rosemary Hall (Wallingford, CT) | | - |
| Sat 2/18 @ 2:30 PM | JV Girls Basketball Game | vs. Kent School (Kent, CT) | | - |
| Sat 2/18 @ 2:30 PM | Varsity Girls Basketball Game | vs. Kent School (Kent, CT)* | | - |
| Sat 2/18 @ 4:00 PM | JV Basketball Game | vs. Trinity-Pawling (Pawling, NY) | | - |
| Mon 2/20 @ 4:30 PM | Varsity Girls Basketball Game | vs. Ethel Walker (Simsbury, CT) | | - |
| Mon 2/20 @ 4:45 PM | Varsity Basketball Game | vs. Berkshire School (Sheffield, MA) | | - |
| Wed 2/22 @ 2:30 PM | JV Basketball Game | vs. Kent School (Kent, CT) | | - |
| Wed 2/22 @ 2:30 PM | Freshman Basketball Game | vs. Trinity-Pawling (Pawling, NY) | | - |
| Wed 2/22 @ 2:30 PM | Varsity Basketball Game | vs. Kent School (Kent, CT)* | | - |
| Wed 2/22 @ 3:00 PM | Varsity Girls Basketball Game | vs. Loomis Chaffee (Windsor, CT) | | - |
| Sat 2/25 @ 1:30 PM | Freshman Basketball Game | vs. Berkshire Country Day (Lenox, MA) | | - |
| Sat 2/25 @ 3:00 PM | JV Girls Basketball Game | vs. Taft (Watertown, CT) | | - |
| Sat 2/25 @ 3:00 PM | Varsity Girls Basketball Game | vs. Taft (Watertown, CT)* | | - |
| Sat 2/25 @ 3:00 PM | Varsity Basketball Game | vs. Loomis Chaffee (Windsor, CT) | | - |