| Tue 5/1 @ 3:45 PM | Freshman Softball Game | vs. Dedham (MA) | | - |
| Wed 5/2 @ TBA | Varsity Baseball Game | vs. Newton North (Newtonville, MA) | | - |
| Wed 5/2 @ 3:45 PM | JV Softball Game | @ Newton North (Newtonville, MA) | | - |
| Wed 5/2 @ 3:45 PM | Varsity Softball Game | @ Newton North (Newtonville, MA) | | - |
| Wed 5/2 @ 4:00 PM | Varsity Lacrosse Game | @ Norwood (MA)* | | - |
| Thu 5/3 @ 3:45 PM | Freshman Softball Game | @ Norwood (MA) | | - |
| Fri 5/4 @ TBA | Varsity Baseball Game | @ Walpole (MA)* | | - |
| Fri 5/4 @ 3:45 PM | JV Softball Game | vs. Walpole (MA) | | - |
| Fri 5/4 @ 3:45 PM | Varsity Softball Game | vs. Walpole (MA)* | | - |
| Sat 5/5 @ 4:00 PM | Varsity Girls Lacrosse Game | @ Billerica Memorial (Billerica, MA) | | - |
| Mon 5/7 @ TBA | Varsity Baseball Game | @ Brookline (MA) | | - |
| Mon 5/7 @ 3:45 PM | JV Softball Game | vs. Brookline (MA) | | - |
| Mon 5/7 @ 3:45 PM | Varsity Softball Game | vs. Brookline (MA) | | - |
| Mon 5/7 @ 4:00 PM | Varsity Girls Lacrosse Game | @ Newton North (Newtonville, MA)* | | - |
| Mon 5/7 @ 4:00 PM | Varsity Softball Game | vs. Brookline (MA) | | - |
| Mon 5/7 @ 4:00 PM | JV Softball Game | vs. Brookline (MA) | | - |
| Tue 5/8 @ 3:45 PM | Freshman Softball Game | @ Wellesley (MA) | | - |
| Wed 5/9 @ TBA | Varsity Baseball Game | vs. Milton (MA)* | | - |
| Wed 5/9 @ 3:45 PM | Varsity Softball Game | @ Milton (MA)* | | - |
| Wed 5/9 @ 3:45 PM | JV Softball Game | @ Milton (MA) | | - |
| Thu 5/10 @ 3:30 PM | JV Girls Lacrosse Game | vs. Martha's Vineyard Regional (Oak Bluffs, MA) | | - |
| Thu 5/10 @ 3:45 PM | JV Softball Game | @ Milton (MA) | | - |
| Thu 5/10 @ 3:45 PM | Freshman Softball Game | vs. Newton North (Newtonville, MA) | | - |
| Thu 5/10 @ 3:45 PM | Varsity Softball Game | @ Milton (MA)* | | - |
| Thu 5/10 @ 7:00 PM | Varsity Baseball Game | vs. Framingham (MA) | | - |
| Fri 5/11 @ 3:45 PM | Freshman Softball Game | vs. Walpole (MA) | | - |
| Mon 5/14 @ 3:45 PM | JV Softball Game | @ Braintree (MA) | | - |
| Mon 5/14 @ 3:45 PM | Varsity Softball Game | @ Braintree (MA) | | - |
| Mon 5/14 @ 4:00 PM | Varsity Lacrosse Game | @ Brookline (MA)* | | - |
| Mon 5/14 @ 7:00 PM | Varsity Baseball Game | vs. Braintree (MA) | | - |
| Tue 5/15 @ 3:45 PM | Freshman Softball Game | @ Brookline (MA) | | - |
| Tue 5/15 @ 3:45 PM | Varsity Softball Game | vs. Randolph (MA) | | - |
| Wed 5/16 @ TBA | Varsity Baseball Game | @ Dedham (MA)* | | - |
| Wed 5/16 @ 3:45 PM | Varsity Softball Game | vs. Dedham (MA)* | | - |
| Wed 5/16 @ 3:45 PM | JV Softball Game | vs. Dedham (MA) | | - |
| Wed 5/16 @ 4:00 PM | Varsity Girls Lacrosse Game | @ Braintree (MA)* | | - |
| Wed 5/16 @ 4:00 PM | JV Girls Lacrosse Game | @ Braintree (MA) | | - |
| Wed 5/16 @ 7:00 PM | Varsity Lacrosse Game | vs. Braintree (MA)* | | - |
| Thu 5/17 @ TBA | Varsity Baseball Game | @ Braintree (MA) | | - |
| Thu 5/17 @ 3:45 PM | Freshman Softball Game | vs. Milton (MA) | | - |
| Thu 5/17 @ 3:45 PM | JV Softball Game | @ Milton (MA) | | - |
| Thu 5/17 @ 3:45 PM | Varsity Softball Game | @ Milton (MA)* | | - |
| Fri 5/18 @ 3:45 PM | Freshman Softball Game | vs. Braintree (MA) | | - |
| Fri 5/18 @ 4:00 PM | JV Softball Game | vs. Randolph (MA) | | - |
| Fri 5/18 @ 6:30 PM | Varsity Softball Game | vs. Randolph (MA) | | - |
| Sat 5/19 @ 10:00 AM | Varsity Girls Lacrosse Game | @ Ursuline Academy (Dedham, MA) | | - |
| Mon 5/21 @ TBA | Varsity Baseball Game | @ Norwood (MA)* | | - |
| Mon 5/21 @ 3:45 PM | Freshman Softball Game | @ Norwood (MA) | | - |
| Mon 5/21 @ 3:45 PM | Varsity Softball Game | @ Norwood (MA)* | | - |
| Mon 5/21 @ 3:45 PM | JV Softball Game | @ Norwood (MA) | | - |
| Mon 5/21 @ 3:45 PM | Varsity Baseball Game | @ Dedham (MA)* | | - |
| Mon 5/21 @ 4:00 PM | Varsity Girls Lacrosse Game | @ Wellesley (MA)* | | - |
| Tue 5/22 @ 3:45 PM | Freshman Softball Game | @ Dedham (MA) | | - |
| Wed 5/23 @ TBA | Varsity Baseball Game | @ Wellesley (MA)* | | - |
| Wed 5/23 @ 3:45 PM | JV Softball Game | @ Wellesley (MA) | | - |
| Wed 5/23 @ 3:45 PM | Varsity Softball Game | @ Wellesley (MA)* | | - |
| Thu 5/24 @ TBA | Varsity Baseball Game | @ Framingham (MA) | | - |
| Thu 5/24 @ 3:45 PM | Freshman Softball Game | vs. Norwood (MA) | | - |
| Fri 5/25 @ TBA | Varsity Baseball Game | @ Hopkinton (MA) | | - |
| Fri 5/25 @ 3:30 PM | Varsity Girls Lacrosse Game | vs. Concord-Carlisle (Concord, MA) | | - |
| Fri 5/25 @ 3:45 PM | Freshman Softball Game | vs. Wellesley (MA) | | - |
| Sat 5/26 @ TBA | Varsity Baseball Game | @ Lincoln-Sudbury (Sudbury, MA) | | - |