| Wed 2/1 @ TBA | Varsity Girls Basketball Game | vs. Lawrence Academy (Groton, MA)* | | - |
| Wed 2/1 @ 4:00 PM | JV Basketball Game | vs. Lawrence Academy (Groton, MA) | | - |
| Wed 2/1 @ 5:30 PM | Varsity Basketball Game | vs. Lawrence Academy (Groton, MA)* | | - |
| Fri 2/3 @ TBA | Varsity Girls Basketball Game | vs. Rivers (Weston, MA)* | | - |
| Fri 2/3 @ 4:30 PM | JV Girls Basketball Game | vs. Rivers (Weston, MA) | | - |
| Fri 2/3 @ 5:30 PM | Varsity Basketball Game | vs. Phillips Academy (Andover, MA)* | | - |
| Sat 2/4 @ TBA | Varsity Basketball Game | vs. St. Mark's (Southborough, MA)* | | - |
| Sat 2/4 @ 1:30 PM | JV Basketball Game | vs. St. Mark's (Southborough, MA) | | - |
| Sat 2/4 @ 1:30 PM | JV Girls Basketball Game | vs. St. Mark's (Southborough, MA) | | - |
| Sat 2/4 @ 3:00 PM | Varsity Girls Basketball Game | vs. St. Mark's (Southborough, MA)* | | - |
| Wed 2/8 @ TBA | Varsity Girls Basketball Game | vs. Middlesex (Concord, MA)* | | - |
| Wed 2/8 @ 3:00 PM | JV Basketball Game | vs. Middlesex (Concord, MA) | | - |
| Wed 2/8 @ 3:30 PM | JV Girls Basketball Game | vs. Middlesex (Concord, MA) | | - |
| Wed 2/8 @ 4:30 PM | Varsity Basketball Game | vs. Middlesex (Concord, MA)* | | - |
| Wed 2/8 @ 4:30 PM | Freshman Basketball Game | vs. Noble & Greenough (Dedham, MA) | | - |
| Fri 2/10 @ TBA | Varsity Basketball Game | vs. Belmont Hill (Belmont, MA)* | | - |
| Fri 2/10 @ 5:00 PM | JV Basketball Game | vs. Belmont Hill (Belmont, MA) | | - |
| Fri 2/10 @ 6:30 PM | Varsity Girls Basketball Game | vs. Tabor Academy (Marion, MA) | | - |
| Fri 2/10 @ 6:30 PM | Varsity Basketball Game | vs. Tabor Academy (Marion, MA) | | - |
| Sat 2/11 @ TBA | Varsity Girls Basketball Game | vs. Tabor Academy (Marion, MA) | | - |
| Wed 2/15 @ 2:15 PM | Freshman Basketball Game | vs. Milton Academy (Milton, MA) | | - |
| Wed 2/15 @ 4:30 PM | Varsity Basketball Game | vs. Buckingham Browne & Nichols (Cambridge, MA)* | | - |
| Wed 2/15 @ 6:00 PM | Varsity Girls Basketball Game | vs. Lawrence Academy (Groton, MA)* | | - |
| Fri 2/17 @ 5:30 PM | JV Girls Basketball Game | vs. Milton Academy (Milton, MA) | | - |
| Fri 2/17 @ 7:00 PM | Varsity Girls Basketball Game | vs. Milton Academy (Milton, MA)* | | - |
| Sat 2/18 @ 2:00 PM | JV Basketball Game | vs. Brooks (North Andover, MA) | | - |
| Sat 2/18 @ 3:30 PM | Varsity Basketball Game | vs. Brooks (North Andover, MA)* | | - |
| Sat 2/18 @ 3:30 PM | Varsity Girls Basketball Game | vs. Brooks (North Andover, MA)* | | - |
| Wed 2/22 @ 3:00 PM | JV Girls Basketball Game | vs. Buckingham Browne & Nichols (Cambridge, MA) | | - |
| Wed 2/22 @ 4:30 PM | Varsity Girls Basketball Game | vs. Buckingham Browne & Nichols (Cambridge, MA)* | | - |
| Wed 2/22 @ 4:30 PM | Varsity Basketball Game | vs. Phillips Exeter Academy (Exeter, NH) | | - |
| Fri 2/24 @ 4:30 PM | JV Basketball Game | vs. Rivers (Weston, MA) | | - |
| Fri 2/24 @ 6:00 PM | Varsity Basketball Game | vs. Rivers (Weston, MA)* | | - |
| Sat 2/25 @ 1:00 PM | JV Girls Basketball Game | vs. Worcester Academy (Worcester, MA) | | - |
| Sat 2/25 @ 2:30 PM | Varsity Girls Basketball Game | vs. Worcester Academy (Worcester, MA) | | - |