| Tue 5/1 @ 3:45 PM | JV Baseball Game | vs. Hand (Madison, CT) | | - |
| Tue 5/1 @ 4:00 PM | JV Softball Game | vs. West Haven (CT) | | - |
| Wed 5/2 @ TBA | Varsity Softball Game | @ Career Magnet (New Haven, CT)* | | - |
| Wed 5/2 @ 3:45 PM | Freshman Baseball Game | @ North Haven (CT) | | - |
| Wed 5/2 @ 7:00 PM | Varsity Baseball Game | @ North Haven (CT)* | | - |
| Wed 5/2 @ 7:00 PM | Varsity Softball Game | @ Career Magnet (New Haven, CT)* | | - |
| Thu 5/3 @ 3:45 PM | JV Baseball Game | vs. North Haven (CT) | | - |
| Fri 5/4 @ 3:30 PM | JV Softball Game | vs. Wilbur Cross (New Haven, CT) | | - |
| Fri 5/4 @ 3:30 PM | Varsity Softball Game | vs. Wilbur Cross (New Haven, CT)* | | - |
| Fri 5/4 @ 3:45 PM | Freshman Baseball Game | @ Shelton (CT) | | - |
| Sat 5/5 @ 8:30 AM | JV Softball Game | vs. Branford (CT) | | - |
| Sat 5/5 @ 10:00 AM | JV Baseball Game | vs. Shelton (CT) | | - |
| Sat 5/5 @ 10:00 AM | JV Softball Game | vs. Branford (CT) | | - |
| Mon 5/7 @ TBA | Varsity Baseball Game | vs. Branford (CT)* | | - |
| Mon 5/7 @ 4:00 PM | Varsity Softball Game | vs. Branford (CT)* | | - |
| Mon 5/7 @ 4:00 PM | JV Softball Game | vs. Branford (CT) | | - |
| Tue 5/8 @ TBA | JV Baseball Game | @ Branford (CT) | | - |
| Tue 5/8 @ TBA | Varsity Softball Game | vs. Wilbur Cross (New Haven, CT)* | | - |
| Tue 5/8 @ 3:45 PM | JV Softball Game | vs. Law (Milford, CT) | | - |
| Tue 5/8 @ 3:45 PM | Varsity Softball Game | @ Platt RVT (Milford, CT) | | - |
| Wed 5/9 @ 3:45 PM | Varsity Baseball Game | @ Career Magnet (New Haven, CT)* | | - |
| Thu 5/10 @ TBA | Varsity Baseball Game | @ Shelton (CT) | | - |
| Thu 5/10 @ TBA | Varsity Softball Game | @ North Haven (CT)* | | - |
| Thu 5/10 @ TBA | JV Baseball Game | vs. Career Magnet (New Haven, CT) | | - |
| Thu 5/10 @ 3:30 PM | JV Softball Game | @ North Haven (CT) | | - |
| Thu 5/10 @ 3:45 PM | JV Baseball Game | vs. Career Magnet (New Haven, CT) | | - |
| Thu 5/10 @ 3:45 PM | JV Softball Game | @ Amity Regional (Woodbridge, CT) | | - |
| Fri 5/11 @ 3:45 PM | Freshman Baseball Game | vs. Wilbur Cross (New Haven, CT) | | - |
| Fri 5/11 @ 3:45 PM | Varsity Baseball Game | vs. Wilbur Cross (New Haven, CT)* | | - |
| Sat 5/12 @ TBA | Varsity Baseball Game | @ Career Magnet (New Haven, CT)* | | - |
| Sat 5/12 @ 10:30 AM | Freshman Baseball Game | @ Shelton (CT) | | - |
| Sat 5/12 @ 10:30 AM | JV Baseball Game | @ Wilbur Cross (New Haven, CT) | | - |
| Mon 5/14 @ TBA | Varsity Softball Game | @ Sacred Heart Academy (Hamden, CT) | | - |
| Mon 5/14 @ 3:45 PM | Varsity Baseball Game | vs. Hamden (CT) | | - |
| Mon 5/14 @ 3:45 PM | Freshman Baseball Game | vs. Hamden (CT) | | - |
| Mon 5/14 @ 3:45 PM | Varsity Softball Game | @ Prince RVT (Hartford, CT) | | - |
| Tue 5/15 @ TBA | Varsity Softball Game | @ Platt RVT (Milford, CT) | | - |
| Tue 5/15 @ 3:45 PM | JV Softball Game | vs. Sheehan (Wallingford, CT) | | - |
| Tue 5/15 @ 3:45 PM | Varsity Softball Game | @ Platt RVT (Milford, CT) | | - |
| Tue 5/15 @ 3:45 PM | JV Baseball Game | @ Hamden (CT) | | - |
| Wed 5/16 @ TBA | Varsity Softball Game | vs. Platt RVT (Milford, CT) | | - |
| Wed 5/16 @ 3:00 PM | Varsity Softball Game | vs. Platt RVT (Milford, CT) | | - |
| Wed 5/16 @ 3:45 PM | Varsity Baseball Game | @ Law (Milford, CT) | | - |
| Wed 5/16 @ 5:00 PM | Varsity Softball Game | vs. Platt RVT (Milford, CT) | | - |
| Thu 5/17 @ 3:45 PM | Varsity Baseball Game | @ Shepaug Valley (Washington, CT) | | - |
| Thu 5/17 @ 3:45 PM | JV Baseball Game | vs. Law (Milford, CT) | | - |
| Thu 5/17 @ 4:00 PM | JV Softball Game | @ Foran (Milford, CT) | | - |
| Thu 5/17 @ 4:00 PM | Varsity Softball Game | @ Foran (Milford, CT) | | - |
| Mon 5/21 @ TBA | Freshman Baseball Game | @ Law (Milford, CT) | | - |
| Mon 5/21 @ TBA | Varsity Softball Game | vs. Cheshire (CT) | | - |
| Mon 5/21 @ 3:45 PM | Freshman Baseball Game | @ Law (Milford, CT) | | - |
| Mon 5/21 @ 3:45 PM | JV Baseball Game | vs. Hand (Madison, CT) | | - |
| Mon 5/21 @ 4:00 PM | JV Softball Game | vs. Cheshire (CT) | | - |