| Wed 2/1 @ TBA | Varsity Girls Basketball Game | vs. Gunnery (Washington, CT)* | | - |
| Wed 2/1 @ 3:00 PM | Varsity Wrestling Game | vs. Brunswick (Greenwich, CT) | | - |
| Wed 2/1 @ 4:00 PM | JV Basketball Game | vs. Berkshire Country Day (Lenox, MA) | | - |
| Wed 2/1 @ 4:00 PM | Varsity Basketball Game | vs. Berkshire School (Sheffield, MA) | | - |
| Wed 2/1 @ 4:00 PM | JV Girls Ice Hockey Game | vs. Simsbury (CT) | | - |
| Wed 2/1 @ 5:30 PM | Varsity Girls Ice Hockey Game | vs. Lawrenceville School (Lawrenceville, NJ) | | - |
| Wed 2/8 @ TBA | Varsity Girls Basketball Game | vs. Cheshire Academy (Cheshire, CT)* | | - |
| Wed 2/8 @ 2:30 PM | Freshman Basketball Game | vs. Hotchkiss (Lakeville, CT) | | - |
| Wed 2/8 @ 3:00 PM | Varsity Wrestling Game | vs. Avon Old Farms (Avon, CT)* | | - |
| Wed 2/8 @ 4:30 PM | Varsity Basketball Game | vs. Hotchkiss (Lakeville, CT)* | | - |
| Wed 2/8 @ 4:30 PM | JV Basketball Game | vs. Hotchkiss (Lakeville, CT) | | - |
| Fri 2/10 @ 4:30 PM | JV Basketball Game | vs. Gunnery (Washington, CT) | | - |
| Fri 2/10 @ 5:00 PM | Varsity Basketball Game | vs. Gunnery (Washington, CT) | | - |
| Sat 2/11 @ 2:30 PM | Freshman Basketball Game | vs. Berkshire Country Day (Lenox, MA) | | - |
| Sat 2/11 @ 3:00 PM | JV Girls Basketball Game | vs. Westminster Academy (Fort Lauderdale, FL) | | - |
| Sat 2/11 @ 7:00 PM | Varsity Girls Basketball Game | vs. Millbrook School (Millbrook, NY) | | - |
| Sat 2/11 @ 7:00 PM | Varsity Basketball Game | vs. Berkshire School (Sheffield, MA) | | - |
| Wed 2/15 @ 2:30 PM | JV Girls Basketball Game | vs. Berkshire Country Day (Lenox, MA) | | - |
| Wed 2/15 @ 2:30 PM | JV Basketball Game | vs. Trinity-Pawling (Pawling, NY) | | - |
| Wed 2/15 @ 2:30 PM | Varsity Girls Basketball Game | vs. Berkshire Country Day (Lenox, MA) | | - |
| Wed 2/15 @ 2:30 PM | Varsity Girls Basketball Game | vs. Berkshire School (Sheffield, MA) | | - |
| Wed 2/15 @ 4:00 PM | Varsity Basketball Game | vs. Trinity-Pawling (Pawling, NY)* | | - |
| Sat 2/18 @ 5:30 PM | JV Basketball Game | vs. Gunnery (Washington, CT) | | - |
| Sat 2/18 @ 7:00 PM | Varsity Basketball Game | vs. Gunnery (Washington, CT) | | - |
| Wed 2/22 @ 2:00 PM | JV Girls Basketball Game | vs. Gunnery (Washington, CT) | | - |
| Wed 2/22 @ 2:00 PM | Freshman Basketball Game | vs. Gunnery (Washington, CT) | | - |
| Wed 2/22 @ 2:45 PM | Varsity Girls Basketball Game | vs. Millbrook School (Millbrook, NY) | | - |
| Sat 2/25 @ 2:30 PM | Freshman Basketball Game | vs. Salisbury School (Salisbury, CT) | | - |
| Sat 2/25 @ 7:30 PM | Varsity Basketball Game | vs. Avon Old Farms (Avon, CT)* | | - |