| Wed 2/1 @ TBA | Varsity Basketball Game | vs. Belmont Hill (Belmont, MA)* | | - |
| Wed 2/1 @ 3:00 PM | JV Basketball Game | vs. Belmont Hill (Belmont, MA) | | - |
| Wed 2/1 @ 3:30 PM | Freshman Basketball Game | vs. Worcester Academy (Worcester, MA) | | - |
| Fri 2/3 @ 4:30 PM | JV Girls Basketball Game | vs. Marianapolis Prep (Thompson, CT) | | - |
| Fri 2/3 @ 4:30 PM | Varsity Girls Basketball Game | vs. Marianapolis Prep (Thompson, CT) | | - |
| Sat 2/4 @ TBA | Varsity Basketball Game | vs. Thayer Academy (Braintree, MA)* | | - |
| Sat 2/4 @ 1:30 PM | JV Basketball Game | vs. Thayer Academy (Braintree, MA) | | - |
| Sat 2/4 @ 1:30 PM | JV Girls Basketball Game | vs. Thayer Academy (Braintree, MA) | | - |
| Sat 2/4 @ 3:00 PM | Varsity Girls Basketball Game | vs. Thayer Academy (Braintree, MA)* | | - |
| Wed 2/8 @ TBA | Varsity Basketball Game | vs. St. Sebastian's Country Day (Needham, MA)* | | - |
| Wed 2/8 @ 2:00 PM | Freshman Basketball Game | vs. Concord Academy (Concord, MA) | | - |
| Wed 2/8 @ 3:45 PM | Varsity Girls Basketball Game | vs. Lawrence Academy (Groton, MA)* | | - |
| Fri 2/10 @ TBA | Varsity Girls Basketball Game | vs. Pomfret School (Pomfret, CT) | | - |
| Sat 2/11 @ 2:30 PM | JV Girls Basketball Game | vs. Governor's Academy (Byfield, MA) | | - |
| Sat 2/11 @ 2:30 PM | Freshman Basketball Game | vs. St. George's (Middletown, RI) | | - |
| Sat 2/11 @ 4:00 PM | Varsity Basketball Game | vs. Governor's Academy (Byfield, MA)* | | - |
| Sat 2/11 @ 4:00 PM | Varsity Girls Basketball Game | vs. Governor's Academy (Byfield, MA)* | | - |
| Sun 2/12 @ TBA | Varsity Basketball Game | vs. Governor's Academy (Byfield, MA)* | | - |
| Wed 2/15 @ 3:15 PM | JV Girls Basketball Game | vs. Noble & Greenough (Dedham, MA) | | - |
| Wed 2/15 @ 3:30 PM | JV Basketball Game | vs. Noble & Greenough (Dedham, MA) | | - |
| Wed 2/15 @ 3:30 PM | Freshman Basketball Game | vs. Noble & Greenough (Dedham, MA) | | - |
| Wed 2/15 @ 4:45 PM | Varsity Girls Basketball Game | vs. Noble & Greenough (Dedham, MA)* | | - |
| Fri 2/17 @ 4:00 PM | Freshman Basketball Game | vs. Lawrence Academy (Groton, MA) | | - |
| Fri 2/17 @ 5:00 PM | Varsity Basketball Game | vs. Marianapolis Prep (Thompson, CT)* | | - |
| Sat 2/18 @ 2:30 PM | JV Girls Basketball Game | vs. St. George's (Middletown, RI) | | - |
| Sat 2/18 @ 2:30 PM | Varsity Girls Basketball Game | vs. St. George's (Middletown, RI)* | | - |
| Wed 2/22 @ 3:15 PM | JV Basketball Game | vs. Brooks (North Andover, MA) | | - |
| Wed 2/22 @ 3:15 PM | Varsity Basketball Game | vs. Brooks (North Andover, MA)* | | - |
| Wed 2/22 @ 4:00 PM | Varsity Girls Basketball Game | vs. Brooks (North Andover, MA)* | | - |
| Sat 2/25 @ 1:45 PM | JV Basketball Game | vs. Groton School (Groton, MA) | | - |
| Sat 2/25 @ 1:45 PM | Varsity Girls Basketball Game | vs. Groton School (Groton, MA)* | | - |
| Sat 2/25 @ 3:45 PM | JV Girls Basketball Game | vs. Groton School (Groton, MA) | | - |