| Tue 5/1 @ TBA | JV Softball Game | vs. Leominster (MA)* | | - |
| Tue 5/1 @ 3:30 PM | Varsity Lacrosse Game | @ Westborough (MA)* | | - |
| Tue 5/1 @ 4:00 PM | Varsity Baseball Game | @ Leominster (MA)* | | - |
| Tue 5/1 @ 4:00 PM | Freshman Baseball Game | @ Leominster (MA) | | - |
| Tue 5/1 @ 4:00 PM | JV Baseball Game | vs. Leominster (MA) | | - |
| Wed 5/2 @ 4:00 PM | Freshman Girls Lacrosse Game | @ Chelmsford (North Chelmsford, MA) | | - |
| Thu 5/3 @ 4:00 PM | Varsity Baseball Game | @ Leominster (MA)* | | - |
| Thu 5/3 @ 4:00 PM | Varsity Girls Lacrosse Game | vs. Groton-Dunstable (Groton, MA)* | | - |
| Thu 5/3 @ 4:00 PM | JV Baseball Game | vs. Leominster (MA) | | - |
| Fri 5/4 @ TBA | JV Softball Game | @ Shrewsbury (MA)* | | - |
| Fri 5/4 @ TBA | Varsity Baseball Game | @ Shrewsbury (MA)* | | - |
| Fri 5/4 @ 4:00 PM | Varsity Boys Volleyball Game | vs. Wachusett Regional (Holden, MA)* | | - |
| Sat 5/5 @ TBA | Varsity Baseball Game | @ Leominster (MA)* | | - |
| Sat 5/5 @ 4:00 PM | Varsity Lacrosse Game | @ Hingham (MA) | | - |
| Mon 5/7 @ TBA | Varsity Baseball Game | @ Marlborough (MA) | | - |
| Mon 5/7 @ TBA | JV Softball Game | vs. Marlborough (MA) | | - |
| Mon 5/7 @ 4:00 PM | Freshman Baseball Game | @ Marlborough (MA) | | - |
| Mon 5/7 @ 4:00 PM | Varsity Girls Lacrosse Game | vs. Westborough (MA)* | | - |
| Tue 5/8 @ 4:00 PM | Varsity Lacrosse Game | vs. Wachusett Regional (Holden, MA)* | | - |
| Tue 5/8 @ 4:00 PM | Varsity Girls Lacrosse Game | @ Wachusett Regional (Holden, MA)* | | - |
| Wed 5/9 @ TBA | Varsity Baseball Game | @ Milford (MA)* | | - |
| Wed 5/9 @ TBA | JV Softball Game | vs. Milford (MA)* | | - |
| Wed 5/9 @ 4:00 PM | Freshman Baseball Game | @ Milford (MA) | | - |
| Thu 5/10 @ 4:00 PM | Varsity Girls Lacrosse Game | vs. Westford Academy (Westford, MA) | | - |
| Fri 5/11 @ TBA | Varsity Baseball Game | @ Fitchburg (MA)* | | - |
| Fri 5/11 @ TBA | JV Softball Game | vs. Fitchburg (MA)* | | - |
| Fri 5/11 @ 4:00 PM | Varsity Boys Volleyball Game | @ Milford (MA)* | | - |
| Mon 5/14 @ TBA | JV Softball Game | @ North Middlesex Regional (Townsend, MA)* | | - |
| Mon 5/14 @ 3:30 PM | Freshman Baseball Game | vs. Westborough (MA) | | - |
| Mon 5/14 @ 4:00 PM | Freshman Baseball Game | vs. North Middlesex Regional (Townsend, MA) | | - |
| Mon 5/14 @ 6:00 PM | Varsity Boys Volleyball Game | @ Medfield (MA) | | - |
| Tue 5/15 @ 4:00 PM | Varsity Girls Lacrosse Game | @ Nashoba Regional (Bolton, MA)* | | - |
| Tue 5/15 @ 4:00 PM | Varsity Baseball Game | vs. North Middlesex Regional (Townsend, MA)* | | - |
| Tue 5/15 @ 4:00 PM | JV Baseball Game | @ North Middlesex Regional (Townsend, MA) | | - |
| Tue 5/15 @ 4:00 PM | Varsity Lacrosse Game | vs. Nashoba Regional (Bolton, MA)* | | - |
| Wed 5/16 @ TBA | JV Softball Game | vs. Wachusett Regional (Holden, MA)* | | - |
| Wed 5/16 @ TBA | Varsity Baseball Game | @ Wachusett Regional (Holden, MA)* | | - |
| Wed 5/16 @ 4:00 PM | Varsity Lacrosse Game | vs. Nashoba Regional (Bolton, MA)* | | - |
| Thu 5/17 @ TBA | Varsity Baseball Game | @ North Middlesex Regional (Townsend, MA)* | | - |
| Thu 5/17 @ TBA | JV Softball Game | @ Leominster (MA)* | | - |
| Thu 5/17 @ 4:00 PM | JV Baseball Game | @ Leominster (MA) | | - |
| Thu 5/17 @ 4:00 PM | Varsity Lacrosse Game | @ Shrewsbury (MA)* | | - |
| Thu 5/17 @ 4:00 PM | Varsity Girls Lacrosse Game | vs. Shrewsbury (MA)* | | - |
| Thu 5/17 @ 6:30 PM | Varsity Boys Volleyball Game | vs. Millis (MA) | | - |
| Fri 5/18 @ TBA | Varsity Baseball Game | @ Leominster (MA)* | | - |
| Sat 5/19 @ 10:00 AM | Freshman Baseball Game | vs. Westborough (MA) | | - |
| Sat 5/19 @ 1:00 PM | Freshman Baseball Game | vs. Westborough (MA) | | - |
| Sat 5/19 @ 3:00 PM | Varsity Girls Lacrosse Game | @ Nipmuc Regional (Upton, MA)* | | - |
| Mon 5/21 @ TBA | JV Softball Game | vs. Shrewsbury (MA)* | | - |
| Mon 5/21 @ TBA | Varsity Baseball Game | @ Shrewsbury (MA)* | | - |
| Mon 5/21 @ 4:00 PM | Varsity Lacrosse Game | vs. North Middlesex Regional (Townsend, MA)* | | - |
| Mon 5/21 @ 4:00 PM | Varsity Girls Lacrosse Game | @ North Middlesex Regional (Townsend, MA)* | | - |
| Mon 5/21 @ 4:00 PM | Freshman Girls Lacrosse Game | @ Lexington (MA) | | - |
| Tue 5/22 @ 3:30 PM | Freshman Baseball Game | @ Nashoba Regional (Bolton, MA) | | - |
| Wed 5/23 @ TBA | Varsity Baseball Game | vs. Marlborough (MA) | | - |
| Wed 5/23 @ TBA | JV Softball Game | @ Marlborough (MA) | | - |
| Wed 5/23 @ 3:30 PM | Varsity Girls Lacrosse Game | vs. Westborough (MA)* | | - |
| Wed 5/23 @ 4:00 PM | Freshman Baseball Game | vs. Marlborough (MA) | | - |
| Wed 5/23 @ 4:00 PM | Varsity Lacrosse Game | vs. Westborough (MA)* | | - |
| Fri 5/25 @ TBA | Varsity Baseball Game | @ St. John's (Shrewsbury, MA) | | - |
| Fri 5/25 @ 3:30 PM | Freshman Baseball Game | @ St. John's (Shrewsbury, MA) | | - |