| Tue 5/1 @ TBA | JV Baseball Game | @ Branford (CT) | | - |
| Tue 5/1 @ 4:00 PM | JV Baseball Game | @ Branford (CT) | | - |
| Wed 5/2 @ TBA | Varsity Softball Game | vs. Hand (Madison, CT)* | | - |
| Wed 5/2 @ TBA | Varsity Baseball Game | vs. Guilford (CT)* | | - |
| Wed 5/2 @ 4:00 PM | Varsity Softball Game | vs. Hand (Madison, CT)* | | - |
| Wed 5/2 @ 4:00 PM | JV Softball Game | vs. Hand (Madison, CT) | | - |
| Thu 5/3 @ 3:45 PM | JV Baseball Game | @ Guilford (CT) | | - |
| Fri 5/4 @ 3:45 PM | Varsity Softball Game | @ Foran (Milford, CT)* | | - |
| Sat 5/5 @ 10:30 AM | JV Softball Game | @ Sheehan (Wallingford, CT) | | - |
| Sat 5/5 @ 12:00 PM | JV Softball Game | @ Sheehan (Wallingford, CT) | | - |
| Mon 5/7 @ TBA | Varsity Baseball Game | @ Hand (Madison, CT)* | | - |
| Mon 5/7 @ TBA | Varsity Softball Game | vs. Hillhouse (New Haven, CT)* | | - |
| Mon 5/7 @ 3:45 PM | JV Softball Game | vs. Hillhouse (New Haven, CT) | | - |
| Mon 5/7 @ 3:45 PM | Varsity Softball Game | vs. Hillhouse (New Haven, CT)* | | - |
| Tue 5/8 @ 3:45 PM | JV Softball Game | @ East Haven (CT) | | - |
| Tue 5/8 @ 3:45 PM | JV Baseball Game | vs. Hand (Madison, CT) | | - |
| Wed 5/9 @ 3:45 PM | Freshman Baseball Game | vs. Notre Dame (West Haven, CT) | | - |
| Wed 5/9 @ 3:45 PM | JV Softball Game | @ Guilford (CT) | | - |
| Wed 5/9 @ 7:00 PM | Varsity Softball Game | @ Guilford (CT)* | | - |
| Thu 5/10 @ 3:45 PM | Varsity Baseball Game | vs. Foran (Milford, CT)* | | - |
| Thu 5/10 @ 3:45 PM | JV Baseball Game | @ Notre Dame (West Haven, CT) | | - |
| Thu 5/10 @ 3:45 PM | JV Softball Game | @ Foran (Milford, CT) | | - |
| Thu 5/10 @ 3:45 PM | Freshman Baseball Game | @ Foran (Milford, CT) | | - |
| Fri 5/11 @ TBA | Varsity Softball Game | @ Hamden (CT) | | - |
| Fri 5/11 @ 3:45 PM | JV Baseball Game | @ Foran (Milford, CT) | | - |
| Sat 5/12 @ TBA | Varsity Softball Game | @ Guilford (CT)* | | - |
| Sat 5/12 @ 10:30 AM | JV Softball Game | @ Guilford (CT) | | - |
| Sat 5/12 @ 10:30 AM | Varsity Baseball Game | vs. Notre Dame (West Haven, CT) | | - |
| Sat 5/12 @ 10:30 AM | Varsity Softball Game | @ Guilford (CT)* | | - |
| Mon 5/14 @ TBA | Varsity Softball Game | vs. Sheehan (Wallingford, CT) | | - |
| Mon 5/14 @ TBA | Varsity Baseball Game | @ Cheshire (CT) | | - |
| Mon 5/14 @ 4:00 PM | Freshman Baseball Game | @ Cheshire (CT) | | - |
| Mon 5/14 @ 4:00 PM | JV Softball Game | vs. Sheehan (Wallingford, CT) | | - |
| Mon 5/14 @ 4:00 PM | Varsity Softball Game | vs. Sheehan (Wallingford, CT) | | - |
| Tue 5/15 @ TBA | JV Baseball Game | vs. Cheshire (CT) | | - |
| Tue 5/15 @ 3:45 PM | JV Softball Game | @ Hamden (CT) | | - |
| Tue 5/15 @ 3:45 PM | Freshman Baseball Game | @ Foran (Milford, CT) | | - |
| Tue 5/15 @ 4:00 PM | JV Baseball Game | vs. Cheshire (CT) | | - |
| Tue 5/15 @ 5:00 PM | Freshman Baseball Game | @ Foran (Milford, CT) | | - |
| Wed 5/16 @ TBA | Varsity Softball Game | @ North Haven (CT) | | - |
| Wed 5/16 @ 3:45 PM | JV Softball Game | @ North Haven (CT) | | - |
| Wed 5/16 @ 3:45 PM | Varsity Baseball Game | vs. East Haven (CT) | | - |
| Wed 5/16 @ 7:00 PM | Varsity Softball Game | @ North Haven (CT) | | - |
| Thu 5/17 @ TBA | Varsity Baseball Game | vs. Foran (Milford, CT)* | | - |
| Thu 5/17 @ 3:45 PM | Freshman Baseball Game | @ Foran (Milford, CT) | | - |
| Thu 5/17 @ 3:45 PM | JV Baseball Game | @ East Haven (CT) | | - |
| Fri 5/18 @ TBA | Varsity Baseball Game | vs. Xavier (Middletown, CT) | | - |
| Fri 5/18 @ TBA | Varsity Softball Game | @ Sacred Heart Academy (Hamden, CT) | | - |
| Fri 5/18 @ 3:45 PM | Freshman Baseball Game | vs. Xavier (Middletown, CT) | | - |
| Fri 5/18 @ 3:45 PM | Varsity Softball Game | @ Sacred Heart Academy (Hamden, CT) | | - |
| Fri 5/18 @ 3:45 PM | JV Softball Game | @ Sacred Heart Academy (Hamden, CT) | | - |
| Fri 5/18 @ 3:45 PM | Varsity Softball Game | @ Prince RVT (Hartford, CT) | | - |
| Sat 5/19 @ 10:30 AM | JV Baseball Game | @ Xavier (Middletown, CT) | | - |
| Mon 5/21 @ TBA | Freshman Baseball Game | vs. East Haven (CT) | | - |
| Mon 5/21 @ TBA | JV Baseball Game | vs. Cheshire (CT) | | - |
| Mon 5/21 @ 3:45 PM | Freshman Baseball Game | vs. East Haven (CT) | | - |
| Mon 5/21 @ 4:00 PM | JV Baseball Game | vs. Cheshire (CT) | | - |
| Tue 5/29 @ 3:30 PM | Varsity Baseball Game | @ Notre Dame (West Haven, CT) | | - |
| Wed 5/30 @ TBA | Varsity Softball Game | @ Suffield (West Suffield, CT)*** | | - |