| Wed 5/2 @ 3:45 PM | Varsity Lacrosse Game | vs. Waltham (MA) | | - |
| Wed 5/2 @ 4:00 PM | Freshman Baseball Game | @ Westford Academy (Westford, MA) | | - |
| Wed 5/2 @ 4:00 PM | JV Softball Game | @ Newton South (Newton, MA) | | - |
| Wed 5/2 @ 4:00 PM | Freshman Baseball Game | @ Newton South (Newton, MA) | | - |
| Wed 5/2 @ 4:00 PM | JV Baseball Game | vs. Newton South (Newton, MA) | | - |
| Wed 5/2 @ 4:00 PM | Freshman Softball Game | vs. Westford Academy (Westford, MA) | | - |
| Wed 5/2 @ 4:00 PM | Varsity Softball Game | @ Newton South (Newton, MA)* | | - |
| Wed 5/2 @ 4:00 PM | Varsity Boys Volleyball Game | @ Newton South (Newton, MA)* | | - |
| Wed 5/2 @ 4:00 PM | Varsity Baseball Game | vs. Newton South (Newton, MA)* | | - |
| Thu 5/3 @ 4:00 PM | JV Softball Game | vs. Waltham (MA) | | - |
| Thu 5/3 @ 7:00 PM | Varsity Softball Game | vs. Waltham (MA)* | | - |
| Fri 5/4 @ 4:00 PM | JV Baseball Game | vs. Boston Latin (Boston, MA) | | - |
| Fri 5/4 @ 4:00 PM | Varsity Softball Game | vs. Waltham (MA)* | | - |
| Fri 5/4 @ 4:00 PM | JV Softball Game | vs. Waltham (MA) | | - |
| Fri 5/4 @ 4:00 PM | Varsity Boys Volleyball Game | @ Cambridge Rindge & Latin (Cambridge, MA)* | | - |
| Fri 5/4 @ 4:00 PM | Freshman Baseball Game | @ Acton-Boxborough (Acton, MA) | | - |
| Fri 5/4 @ 4:00 PM | Varsity Baseball Game | vs. Boston Latin (Boston, MA)* | | - |
| Sat 5/5 @ 5:00 PM | Varsity Lacrosse Game | @ Cohasset (MA) | | - |
| Sun 5/6 @ TBA | Varsity Baseball Game | @ Boston Latin (Boston, MA)* | | - |
| Mon 5/7 @ TBA | Varsity Baseball Game | @ Westford Academy (Westford, MA)* | | - |
| Mon 5/7 @ 4:00 PM | JV Softball Game | vs. Boston Latin (Boston, MA) | | - |
| Mon 5/7 @ 4:00 PM | Freshman Baseball Game | vs. Westford Academy (Westford, MA) | | - |
| Mon 5/7 @ 4:00 PM | Varsity Softball Game | vs. Boston Latin (Boston, MA)* | | - |
| Mon 5/7 @ 4:00 PM | JV Baseball Game | @ Westford Academy (Westford, MA) | | - |
| Tue 5/8 @ 4:00 PM | Freshman Baseball Game | @ Acton-Boxborough (Acton, MA) | | - |
| Tue 5/8 @ 5:00 PM | Varsity Lacrosse Game | @ Peabody Veterans Memorial (Peabody, MA) | | - |
| Wed 5/9 @ 3:45 PM | Freshman Baseball Game | @ Concord-Carlisle (Concord, MA) | | - |
| Wed 5/9 @ 4:00 PM | JV Softball Game | vs. Concord-Carlisle (Concord, MA) | | - |
| Wed 5/9 @ 4:00 PM | Varsity Softball Game | vs. Concord-Carlisle (Concord, MA)* | | - |
| Wed 5/9 @ 4:00 PM | Varsity Baseball Game | vs. Concord-Carlisle (Concord, MA)* | | - |
| Wed 5/9 @ 4:00 PM | JV Baseball Game | vs. Concord-Carlisle (Concord, MA) | | - |
| Thu 5/10 @ 4:00 PM | Freshman Baseball Game | vs. Bedford (MA) | | - |
| Thu 5/10 @ 4:00 PM | Varsity Baseball Game | vs. Weston (MA)* | | - |
| Thu 5/10 @ 4:00 PM | Varsity Softball Game | @ Bedford (MA)* | | - |
| Thu 5/10 @ 4:00 PM | JV Softball Game | @ Bedford (MA) | | - |
| Thu 5/10 @ 5:00 PM | Varsity Baseball Game | vs. Weston (MA)* | | - |
| Thu 5/10 @ 6:00 PM | Varsity Lacrosse Game | @ Acton-Boxborough (Acton, MA)* | | - |
| Fri 5/11 @ TBA | Varsity Baseball Game | @ Concord-Carlisle (Concord, MA)* | | - |
| Fri 5/11 @ 4:00 PM | JV Softball Game | vs. Concord-Carlisle (Concord, MA) | | - |
| Fri 5/11 @ 4:00 PM | JV Baseball Game | vs. Concord-Carlisle (Concord, MA) | | - |
| Fri 5/11 @ 4:00 PM | Freshman Softball Game | vs. Concord-Carlisle (Concord, MA) | | - |
| Fri 5/11 @ 4:00 PM | Varsity Boys Volleyball Game | vs. Westford Academy (Westford, MA)* | | - |
| Fri 5/11 @ 4:00 PM | Varsity Softball Game | vs. Concord-Carlisle (Concord, MA)* | | - |
| Fri 5/11 @ 4:00 PM | Freshman Baseball Game | @ Acton-Boxborough (Acton, MA) | | - |
| Sat 5/12 @ TBA | Varsity Baseball Game | @ Whitman-Hanson Regional (Whitman, MA) | | - |
| Sat 5/12 @ 12:00 PM | JV Baseball Game | @ Whitman-Hanson Regional (Whitman, MA) | | - |
| Sat 5/12 @ 5:00 PM | Varsity Lacrosse Game | vs. St. John's Prep (Danvers, MA) | | - |
| Mon 5/14 @ TBA | Varsity Baseball Game | @ Acton-Boxborough (Acton, MA)* | | - |
| Mon 5/14 @ 4:00 PM | JV Baseball Game | vs. Acton-Boxborough (Acton, MA) | | - |
| Mon 5/14 @ 4:00 PM | JV Softball Game | vs. Westford Academy (Westford, MA) | | - |
| Mon 5/14 @ 4:00 PM | Varsity Softball Game | vs. Westford Academy (Westford, MA)* | | - |
| Mon 5/14 @ 4:00 PM | Freshman Baseball Game | @ Acton-Boxborough (Acton, MA) | | - |
| Mon 5/14 @ 4:30 PM | JV Girls Lacrosse Game | @ Norwell (MA) | | - |
| Tue 5/15 @ 4:00 PM | Freshman Softball Game | @ Westford Academy (Westford, MA) | | - |
| Tue 5/15 @ 5:00 PM | Freshman Softball Game | @ Westford Academy (Westford, MA) | | - |
| Wed 5/16 @ 3:45 PM | Varsity Softball Game | vs. Acton-Boxborough (Acton, MA)* | | - |
| Wed 5/16 @ 3:45 PM | JV Softball Game | vs. Abby Kelley Foster (Worcester, MA) | | - |
| Wed 5/16 @ 4:00 PM | Freshman Softball Game | @ Waltham (MA) | | - |
| Wed 5/16 @ 4:00 PM | Freshman Softball Game | vs. Westford Academy (Westford, MA) | | - |
| Wed 5/16 @ 4:00 PM | JV Softball Game | vs. Abby Kelley Foster (Worcester, MA) | | - |
| Wed 5/16 @ 4:00 PM | Freshman Baseball Game | vs. Newton South (Newton, MA) | | - |
| Wed 5/16 @ 7:00 PM | Varsity Softball Game | vs. Acton-Boxborough (Acton, MA)* | | - |
| Thu 5/17 @ TBA | Varsity Baseball Game | @ Newton South (Newton, MA)* | | - |
| Thu 5/17 @ 4:00 PM | Varsity Softball Game | vs. Newton South (Newton, MA)* | | - |
| Thu 5/17 @ 4:00 PM | JV Baseball Game | @ Newton South (Newton, MA) | | - |
| Thu 5/17 @ 4:00 PM | JV Softball Game | vs. Newton South (Newton, MA) | | - |
| Thu 5/17 @ 4:00 PM | Freshman Baseball Game | vs. Westford Academy (Westford, MA) | | - |
| Thu 5/17 @ 5:00 PM | Varsity Lacrosse Game | @ Newton South (Newton, MA)* | | - |
| Fri 5/18 @ TBA | Varsity Baseball Game | vs. Westford Academy (Westford, MA)* | | - |
| Fri 5/18 @ 4:00 PM | Freshman Softball Game | vs. Concord-Carlisle (Concord, MA) | | - |
| Fri 5/18 @ 4:00 PM | Varsity Boys Volleyball Game | vs. Newton South (Newton, MA)* | | - |
| Fri 5/18 @ 4:00 PM | JV Baseball Game | vs. Westford Academy (Westford, MA) | | - |
| Sat 5/19 @ TBA | Varsity Baseball Game | @ Weston (MA)* | | - |
| Sat 5/19 @ 5:30 PM | Varsity Lacrosse Game | @ Cheshire (CT) | | - |
| Mon 5/21 @ TBA | Varsity Baseball Game | @ Boston Latin (Boston, MA)* | | - |
| Mon 5/21 @ 4:00 PM | JV Baseball Game | @ Boston Latin (Boston, MA) | | - |
| Mon 5/21 @ 4:00 PM | Freshman Softball Game | @ Westford Academy (Westford, MA) | | - |
| Mon 5/21 @ 4:00 PM | Freshman Baseball Game | vs. Acton-Boxborough (Acton, MA) | | - |
| Mon 5/21 @ 4:30 PM | JV Girls Lacrosse Game | @ Norwell (MA) | | - |
| Mon 5/21 @ 5:00 PM | Varsity Boys Volleyball Game | @ Xaverian Brothers (Westwood, MA) | | - |
| Mon 5/21 @ 9:00 PM | Freshman Softball Game | @ Westford Academy (Westford, MA) | | - |
| Tue 5/22 @ 4:00 PM | Freshman Baseball Game | vs. Westford Academy (Westford, MA) | | - |
| Wed 5/23 @ 4:00 PM | Freshman Softball Game | vs. Waltham (MA) | | - |
| Wed 5/23 @ 4:00 PM | Varsity Softball Game | @ Boston Latin (Boston, MA)* | | - |
| Wed 5/23 @ 4:00 PM | JV Softball Game | @ Boston Latin (Boston, MA) | | - |
| Wed 5/23 @ 4:00 PM | Freshman Baseball Game | @ Westford Academy (Westford, MA) | | - |
| Wed 5/23 @ 7:00 PM | Varsity Lacrosse Game | @ Andover (MA) | | - |
| Thu 5/24 @ 4:00 PM | JV Softball Game | vs. Newton South (Newton, MA) | | - |
| Thu 5/24 @ 4:00 PM | Freshman Baseball Game | vs. Wayland (MA) | | - |
| Thu 5/24 @ 4:00 PM | Varsity Girls Lacrosse Game | @ Winchester (MA) | | - |
| Fri 5/25 @ TBA | Varsity Baseball Game | @ Franklin (MA) | | - |
| Fri 5/25 @ 4:00 PM | JV Softball Game | vs. Acton-Boxborough (Acton, MA) | | - |
| Fri 5/25 @ 4:00 PM | Varsity Baseball Game | vs. Hopkinton (MA) | | - |
| Fri 5/25 @ 4:00 PM | Varsity Softball Game | vs. Acton-Boxborough (Acton, MA)* | | - |
| Sat 5/26 @ TBA | Varsity Baseball Game | @ Natick (MA) | | - |
| Sat 5/26 @ 4:00 PM | Freshman Softball Game | vs. Waltham (MA) | | - |
| Tue 5/29 @ 4:00 PM | Freshman Baseball Game | vs. Waltham (MA) | | - |
| Tue 5/29 @ 4:00 PM | Freshman Softball Game | vs. Waltham (MA) | | - |
| Wed 5/30 @ 2:00 PM | Varsity Girls Lacrosse Game | vs. Haverhill (MA) | | - |