| Wed 2/1 @ TBA | Varsity Basketball Game | vs. Phillips Exeter Academy (Exeter, NH)* | | - |
| Fri 2/3 @ TBA | Varsity Girls Basketball Game | vs. Worcester Academy (Worcester, MA)* | | - |
| Fri 2/3 @ 6:00 PM | Varsity Basketball Game | vs. Worcester Academy (Worcester, MA)* | | - |
| Sat 2/4 @ TBA | Varsity Girls Basketball Game | vs. Milton Academy (Milton, MA) | | - |
| Sat 2/4 @ TBA | Varsity Basketball Game | vs. Belmont Hill (Belmont, MA) | | - |
| Sat 2/4 @ 2:00 PM | Varsity Basketball Game | vs. Milton Academy (Milton, MA) | | - |
| Wed 2/8 @ TBA | Varsity Girls Basketball Game | vs. Phillips Academy (Andover, MA)* | | - |
| Wed 2/8 @ 3:30 PM | Freshman Girls Basketball Game | vs. Dana Hall (Wellesley, MA) | | - |
| Wed 2/8 @ 3:30 PM | Varsity Basketball Game | vs. Phillips Academy (Andover, MA)* | | - |
| Fri 2/10 @ 4:45 PM | JV Basketball Game | vs. St. George's (Middletown, RI) | | - |
| Fri 2/10 @ 6:30 PM | Varsity Basketball Game | vs. Thayer Academy (Braintree, MA) | | - |
| Fri 2/10 @ 6:30 PM | Varsity Girls Basketball Game | vs. Thayer Academy (Braintree, MA) | | - |
| Sat 2/11 @ TBA | Varsity Girls Basketball Game | vs. Thayer Academy (Braintree, MA) | | - |
| Wed 2/15 @ 4:00 PM | Varsity Basketball Game | vs. Worcester Academy (Worcester, MA)* | | - |
| Wed 2/15 @ 4:00 PM | Varsity Girls Basketball Game | vs. Worcester Academy (Worcester, MA)* | | - |
| Sat 2/18 @ 2:00 PM | Varsity Basketball Game | vs. Deerfield Academy (Deerfield, MA)* | | - |
| Sat 2/18 @ 4:30 PM | Varsity Basketball Game | vs. Loomis Chaffee (Windsor, CT)* | | - |
| Sat 2/18 @ 4:30 PM | Varsity Girls Basketball Game | vs. Loomis Chaffee (Windsor, CT)* | | - |
| Mon 2/20 @ 5:00 PM | Varsity Girls Basketball Game | vs. Naval Academy Prep (Newport, RI) | | - |
| Wed 2/22 @ 3:30 PM | Varsity Basketball Game | vs. Buckingham Browne & Nichols (Cambridge, MA) | | - |
| Wed 2/22 @ 4:00 PM | JV Basketball Game | vs. Rivers (Weston, MA) | | - |
| Sat 2/25 @ 2:30 PM | Varsity Girls Basketball Game | vs. Northfield Mount Hermon (Mount Hermon, MA)* | | - |
| Sat 2/25 @ 4:30 PM | Varsity Basketball Game | vs. Cushing Academy (Ashburnham, MA)* | | - |