| Tue 5/1 @ 3:45 PM | Freshman Softball Game | vs. Walpole (MA) | | - |
| Tue 5/1 @ 7:00 PM | Freshman Girls Lacrosse Game | vs. Walpole (MA) | | - |
| Wed 5/2 @ 3:30 PM | Freshman Girls Lacrosse Game | @ Governor's Academy (Byfield, MA) | | - |
| Wed 5/2 @ 3:45 PM | JV Softball Game | @ Framingham (MA) | | - |
| Wed 5/2 @ 3:45 PM | Freshman Softball Game | vs. Walpole (MA) | | - |
| Wed 5/2 @ 3:45 PM | Varsity Baseball Game | @ Dedham (MA)* | | - |
| Wed 5/2 @ 3:45 PM | Varsity Softball Game | @ Framingham (MA) | | - |
| Wed 5/2 @ 3:45 PM | Varsity Baseball Game | vs. Framingham (MA) | | - |
| Wed 5/2 @ 4:00 PM | Varsity Lacrosse Game | vs. Wellesley (MA)* | | - |
| Thu 5/3 @ 3:45 PM | Freshman Softball Game | @ Wellesley (MA) | | - |
| Thu 5/3 @ 4:00 PM | Freshman Girls Lacrosse Game | vs. Needham (MA) | | - |
| Fri 5/4 @ 3:45 PM | JV Softball Game | vs. Norwood (MA) | | - |
| Fri 5/4 @ 3:45 PM | Varsity Softball Game | vs. Norwood (MA)* | | - |
| Fri 5/4 @ 7:00 PM | Varsity Girls Lacrosse Game | vs. Weymouth (South Weymouth, MA)* | | - |
| Fri 5/4 @ 7:00 PM | Varsity Baseball Game | @ Norwood (MA)* | | - |
| Sat 5/5 @ 3:00 PM | Varsity Girls Lacrosse Game | @ Governor's Academy (Byfield, MA) | | - |
| Mon 5/7 @ TBA | Varsity Baseball Game | vs. Needham (MA) | | - |
| Mon 5/7 @ 3:45 PM | Varsity Softball Game | @ Needham (MA) | | - |
| Mon 5/7 @ 3:45 PM | JV Softball Game | @ Needham (MA) | | - |
| Mon 5/7 @ 4:00 PM | Varsity Lacrosse Game | vs. Framingham (MA)* | | - |
| Mon 5/7 @ 4:00 PM | Varsity Girls Lacrosse Game | @ Framingham (MA)* | | - |
| Mon 5/7 @ 4:30 PM | JV Softball Game | @ Needham (MA) | | - |
| Mon 5/7 @ 6:30 PM | Varsity Softball Game | @ Needham (MA) | | - |
| Tue 5/8 @ TBA | Varsity Baseball Game | @ Norwood (MA)* | | - |
| Tue 5/8 @ 3:45 PM | Freshman Softball Game | @ Dedham (MA) | | - |
| Tue 5/8 @ 4:00 PM | Freshman Girls Lacrosse Game | @ Framingham (MA) | | - |
| Wed 5/9 @ TBA | Varsity Baseball Game | @ Natick (MA)* | | - |
| Wed 5/9 @ 3:15 PM | Varsity Girls Lacrosse Game | @ Phillips Academy (Andover, MA) | | - |
| Wed 5/9 @ 3:45 PM | Varsity Softball Game | vs. Natick (MA)* | | - |
| Wed 5/9 @ 3:45 PM | JV Softball Game | vs. Natick (MA) | | - |
| Wed 5/9 @ 4:00 PM | JV Girls Lacrosse Game | vs. Walpole (MA) | | - |
| Wed 5/9 @ 7:15 PM | Varsity Lacrosse Game | @ Walpole (MA)* | | - |
| Thu 5/10 @ 3:45 PM | Varsity Softball Game | vs. Natick (MA)* | | - |
| Thu 5/10 @ 3:45 PM | JV Softball Game | vs. Natick (MA) | | - |
| Thu 5/10 @ 3:45 PM | Varsity Baseball Game | @ Fenway (Boston, MA) | | - |
| Thu 5/10 @ 3:45 PM | Freshman Softball Game | vs. Framingham (MA) | | - |
| Thu 5/10 @ 4:00 PM | Freshman Girls Lacrosse Game | @ Wellesley (MA) | | - |
| Thu 5/10 @ 4:00 PM | Varsity Girls Lacrosse Game | @ Hull (MA) | | - |
| Fri 5/11 @ 3:45 PM | Freshman Softball Game | @ Norwood (MA) | | - |
| Fri 5/11 @ 4:00 PM | Freshman Girls Lacrosse Game | @ Framingham (MA) | | - |
| Mon 5/14 @ TBA | Varsity Baseball Game | vs. Weymouth (South Weymouth, MA) | | - |
| Mon 5/14 @ 3:45 PM | Varsity Softball Game | @ Weymouth (South Weymouth, MA) | | - |
| Mon 5/14 @ 3:45 PM | JV Softball Game | @ Weymouth (South Weymouth, MA) | | - |
| Mon 5/14 @ 4:00 PM | Varsity Girls Lacrosse Game | @ Needham (MA)* | | - |
| Mon 5/14 @ 4:00 PM | Varsity Lacrosse Game | vs. Needham (MA)* | | - |
| Tue 5/15 @ 3:45 PM | Freshman Girls Lacrosse Game | @ Braintree (MA) | | - |
| Tue 5/15 @ 3:45 PM | Varsity Softball Game | vs. Fontbonne Academy (Milton, MA) | | - |
| Tue 5/15 @ 3:45 PM | Freshman Softball Game | vs. Needham (MA) | | - |
| Tue 5/15 @ 3:45 PM | JV Softball Game | vs. Fontbonne Academy (Milton, MA) | | - |
| Tue 5/15 @ 4:00 PM | Freshman Girls Lacrosse Game | @ Newton North (Newtonville, MA) | | - |
| Wed 5/16 @ TBA | Varsity Baseball Game | @ Walpole (MA)* | | - |
| Wed 5/16 @ 3:45 PM | Freshman Softball Game | @ Braintree (MA) | | - |
| Wed 5/16 @ 3:45 PM | Varsity Softball Game | vs. Walpole (MA)* | | - |
| Wed 5/16 @ 3:45 PM | JV Softball Game | vs. Walpole (MA) | | - |
| Wed 5/16 @ 4:00 PM | JV Girls Lacrosse Game | @ Weymouth (South Weymouth, MA) | | - |
| Wed 5/16 @ 7:00 PM | Varsity Lacrosse Game | vs. Weymouth (South Weymouth, MA)* | | - |
| Thu 5/17 @ TBA | Varsity Baseball Game | vs. Fenway (Boston, MA) | | - |
| Thu 5/17 @ 3:45 PM | JV Softball Game | vs. Natick (MA) | | - |
| Thu 5/17 @ 3:45 PM | Varsity Softball Game | vs. Natick (MA)* | | - |
| Thu 5/17 @ 3:45 PM | Freshman Softball Game | @ Natick (MA) | | - |
| Thu 5/17 @ 4:00 PM | JV Girls Lacrosse Game | @ Pembroke (MA) | | - |
| Thu 5/17 @ 4:00 PM | Varsity Lacrosse Game | vs. Weston (MA) | | - |
| Fri 5/18 @ TBA | Varsity Baseball Game | @ Framingham (MA) | | - |
| Fri 5/18 @ 3:45 PM | Freshman Girls Lacrosse Game | @ Braintree (MA) | | - |
| Fri 5/18 @ 3:45 PM | Freshman Softball Game | vs. Weymouth (South Weymouth, MA) | | - |
| Fri 5/18 @ 4:00 PM | JV Girls Lacrosse Game | @ Weymouth (South Weymouth, MA) | | - |
| Sat 5/19 @ 12:30 PM | Varsity Girls Lacrosse Game | @ Hull (MA) | | - |
| Sat 5/19 @ 7:00 PM | Varsity Lacrosse Game | vs. Canton (MA) | | - |
| Mon 5/21 @ TBA | Varsity Baseball Game | vs. Wellesley (MA)* | | - |
| Mon 5/21 @ 3:45 PM | Freshman Girls Lacrosse Game | @ Hingham (MA) | | - |
| Mon 5/21 @ 7:00 PM | Varsity Lacrosse Game | @ Dedham (MA)* | | - |
| Mon 5/21 @ 7:00 PM | Varsity Girls Lacrosse Game | vs. Dedham (MA)* | | - |
| Tue 5/22 @ TBA | Varsity Baseball Game | @ Fenway (Boston, MA) | | - |
| Tue 5/22 @ 3:45 PM | Freshman Softball Game | @ Walpole (MA) | | - |
| Wed 5/23 @ 3:45 PM | JV Softball Game | @ Dedham (MA) | | - |
| Wed 5/23 @ 3:45 PM | Varsity Softball Game | @ Dedham (MA)* | | - |
| Wed 5/23 @ 3:45 PM | Varsity Baseball Game | vs. Dedham (MA)* | | - |
| Wed 5/23 @ 3:45 PM | Freshman Softball Game | @ Walpole (MA) | | - |
| Wed 5/23 @ 4:00 PM | Freshman Girls Lacrosse Game | vs. Weymouth (South Weymouth, MA) | | - |
| Wed 5/23 @ 7:00 PM | Varsity Lacrosse Game | @ Scituate (MA) | | - |
| Thu 5/24 @ 3:45 PM | Freshman Softball Game | vs. Wellesley (MA) | | - |
| Fri 5/25 @ TBA | Varsity Baseball Game | vs. Dedham (MA)* | | - |
| Fri 5/25 @ 3:30 PM | Varsity Softball Game | @ Fontbonne Academy (Milton, MA) | | - |
| Fri 5/25 @ 3:30 PM | JV Softball Game | @ Fontbonne Academy (Milton, MA) | | - |
| Fri 5/25 @ 3:45 PM | Freshman Softball Game | vs. Dedham (MA) | | - |
| Fri 5/25 @ 4:00 PM | Freshman Girls Lacrosse Game | @ Walpole (MA) | | - |
| Fri 5/25 @ 4:30 PM | Varsity Baseball Game | vs. Noble & Greenough (Dedham, MA) | | - |
| Sun 5/27 @ TBA | Varsity Baseball Game | vs. Bridgewater-Raynham (Bridgewater, MA) | | - |
| Tue 5/29 @ 3:45 PM | Freshman Softball Game | @ Braintree (MA) | | - |
| Tue 5/29 @ 4:00 PM | Freshman Girls Lacrosse Game | @ Needham (MA) | | - |
| Thu 5/31 @ 3:45 PM | Freshman Softball Game | @ Needham (MA) | | - |