| Tue 5/1 @ 3:30 PM | Freshman Baseball Game | vs. Westborough (MA) | | - |
| Tue 5/1 @ 7:00 PM | Varsity Lacrosse Game | @ Grafton Memorial (Grafton, MA) | | - |
| Wed 5/2 @ 6:00 PM | Varsity Boys Volleyball Game | @ Boston College High (Boston, MA)* | | - |
| Thu 5/3 @ TBA | Varsity Baseball Game | @ St. John's Prep (Danvers, MA) | | - |
| Thu 5/3 @ 6:00 PM | Varsity Boys Volleyball Game | @ Xaverian Brothers (Westwood, MA)* | | - |
| Fri 5/4 @ 3:30 PM | Freshman Baseball Game | vs. Nashoba Regional (Bolton, MA) | | - |
| Fri 5/4 @ 4:00 PM | Varsity Lacrosse Game | vs. St. Bernard's Central Catholic (Fitchburg, MA)* | | - |
| Fri 5/4 @ 6:30 PM | Varsity Boys Volleyball Game | vs. St. John's Prep (Danvers, MA)* | | - |
| Sat 5/5 @ 2:00 PM | Varsity Baseball Game | @ Shrewsbury (MA) | | - |
| Mon 5/7 @ 3:30 PM | Freshman Baseball Game | vs. St. Peter-Marian (Worcester, MA) | | - |
| Mon 5/7 @ 4:00 PM | Varsity Lacrosse Game | @ St. Peter-Marian (Worcester, MA)* | | - |
| Tue 5/8 @ TBA | Varsity Baseball Game | @ St. Peter-Marian (Worcester, MA)* | | - |
| Tue 5/8 @ 3:30 PM | JV Baseball Game | vs. St. Peter-Marian (Worcester, MA) | | - |
| Tue 5/8 @ 3:30 PM | Freshman Baseball Game | vs. St. Peter-Marian (Worcester, MA) | | - |
| Tue 5/8 @ 4:00 PM | Varsity Lacrosse Game | vs. Minnechaug Regional (Wilbraham, MA) | | - |
| Tue 5/8 @ 6:00 PM | Varsity Boys Volleyball Game | vs. Milford (MA) | | - |
| Wed 5/9 @ 4:00 PM | Freshman Baseball Game | @ Boston College High (Boston, MA) | | - |
| Thu 5/10 @ TBA | Varsity Baseball Game | @ Burncoat (Worcester, MA) | | - |
| Fri 5/11 @ 4:00 PM | Varsity Baseball Game | vs. Boston College High (Boston, MA) | | - |
| Fri 5/11 @ 6:30 PM | Varsity Boys Volleyball Game | @ Millis (MA)* | | - |
| Mon 5/14 @ 5:00 PM | Varsity Lacrosse Game | @ Malden Catholic (Malden, MA) | | - |
| Tue 5/15 @ 4:00 PM | Varsity Baseball Game | vs. New Bedford (MA) | | - |
| Tue 5/15 @ 4:00 PM | JV Baseball Game | vs. New Bedford (MA) | | - |
| Wed 5/16 @ TBA | Varsity Baseball Game | @ Burncoat (Worcester, MA) | | - |
| Wed 5/16 @ 3:30 PM | Freshman Baseball Game | vs. Westborough (MA) | | - |
| Wed 5/16 @ 4:30 PM | JV Lacrosse Game | @ Longmeadow (MA) | | - |
| Wed 5/16 @ 4:30 PM | Varsity Lacrosse Game | @ Longmeadow (MA) | | - |
| Fri 5/18 @ TBA | Varsity Baseball Game | @ Doherty Memorial (Worcester, MA) | | - |
| Fri 5/18 @ 6:00 PM | Varsity Boys Volleyball Game | vs. Medfield (MA)* | | - |
| Tue 5/22 @ 3:30 PM | Freshman Baseball Game | vs. Shepherd Hill Regional (Dudley, MA) | | - |
| Wed 5/23 @ 3:30 PM | JV Baseball Game | @ Bishop Feehan (Attleboro, MA) | | - |
| Wed 5/23 @ 3:30 PM | Freshman Baseball Game | vs. Bishop Feehan (Attleboro, MA) | | - |
| Wed 5/23 @ 3:30 PM | Varsity Baseball Game | vs. Bishop Feehan (Attleboro, MA) | | - |
| Wed 5/23 @ 4:00 PM | JV Lacrosse Game | vs. Advanced Math & Science Academy (Marlborough, MA) | | - |
| Fri 5/25 @ TBA | Varsity Baseball Game | @ Algonquin Regional (Northborough, MA) | | - |
| Fri 5/25 @ 3:30 PM | Freshman Baseball Game | vs. Algonquin Regional (Northborough, MA) | | - |
| Sat 5/26 @ TBA | Varsity Baseball Game | @ Wachusett Regional (Holden, MA) | | - |
| Sat 5/26 @ 11:00 AM | JV Baseball Game | vs. Wachusett Regional (Holden, MA) | | - |
| Sat 5/26 @ 11:00 AM | Freshman Baseball Game | vs. Bishop Hendricken (Warwick, RI) | | - |
| Tue 5/29 @ 4:00 PM | Varsity Lacrosse Game | vs. Shepherd Hill Regional (Dudley, MA) | | - |