| Tue 5/1 @ 3:45 PM | JV Baseball Game | vs. Hamden (CT) | | - |
| Wed 5/2 @ 3:45 PM | Varsity Baseball Game | vs. Wilbur Cross (New Haven, CT) | | - |
| Wed 5/2 @ 3:45 PM | Varsity Softball Game | vs. Cheshire (CT)* | | - |
| Wed 5/2 @ 3:45 PM | JV Softball Game | vs. Cheshire (CT) | | - |
| Thu 5/3 @ 3:45 PM | JV Baseball Game | @ Wilbur Cross (New Haven, CT) | | - |
| Fri 5/4 @ 3:45 PM | JV Softball Game | @ Amity Regional (Woodbridge, CT) | | - |
| Fri 5/4 @ 3:45 PM | Varsity Softball Game | @ Amity Regional (Woodbridge, CT)* | | - |
| Fri 5/4 @ 3:45 PM | Freshman Baseball Game | vs. Amity Regional (Woodbridge, CT) | | - |
| Sat 5/5 @ 10:30 AM | JV Baseball Game | @ Amity Regional (Woodbridge, CT) | | - |
| Mon 5/7 @ TBA | Varsity Baseball Game | vs. Sheehan (Wallingford, CT)* | | - |
| Mon 5/7 @ 3:45 PM | Freshman Baseball Game | @ Sheehan (Wallingford, CT) | | - |
| Mon 5/7 @ 3:45 PM | JV Softball Game | vs. Sheehan (Wallingford, CT) | | - |
| Mon 5/7 @ 3:45 PM | Varsity Softball Game | vs. Sheehan (Wallingford, CT)* | | - |
| Mon 5/7 @ 5:30 PM | Varsity Lacrosse Game | vs. Nonnewaug (Woodbury, CT) | | - |
| Tue 5/8 @ TBA | Varsity Baseball Game | vs. Amity Regional (Woodbridge, CT)* | | - |
| Tue 5/8 @ 3:45 PM | Freshman Baseball Game | vs. Amity Regional (Woodbridge, CT) | | - |
| Wed 5/9 @ 3:45 PM | Varsity Softball Game | @ Shelton (CT)* | | - |
| Thu 5/10 @ 3:45 PM | Freshman Baseball Game | vs. Amity Regional (Woodbridge, CT) | | - |
| Thu 5/10 @ 4:00 PM | Varsity Baseball Game | @ Cheshire (CT)* | | - |
| Thu 5/10 @ 4:00 PM | JV Baseball Game | vs. Cheshire (CT) | | - |
| Thu 5/10 @ 4:00 PM | Freshman Baseball Game | @ Cheshire (CT) | | - |
| Fri 5/11 @ TBA | Varsity Baseball Game | @ Shelton (CT)* | | - |
| Fri 5/11 @ 3:45 PM | Freshman Baseball Game | @ Shelton (CT) | | - |
| Fri 5/11 @ 3:45 PM | Varsity Softball Game | vs. Career Magnet (New Haven, CT) | | - |
| Sat 5/12 @ 10:00 AM | JV Baseball Game | vs. Shelton (CT) | | - |
| Sat 5/12 @ 11:00 AM | JV Softball Game | vs. Career Magnet (New Haven, CT) | | - |
| Mon 5/14 @ TBA | Varsity Baseball Game | vs. Guilford (CT) | | - |
| Mon 5/14 @ 3:45 PM | Freshman Baseball Game | vs. Guilford (CT) | | - |
| Tue 5/15 @ TBA | JV Baseball Game | @ Guilford (CT) | | - |
| Tue 5/15 @ 3:45 PM | JV Baseball Game | @ Guilford (CT) | | - |
| Tue 5/15 @ 4:00 PM | JV Softball Game | @ Foran (Milford, CT) | | - |
| Tue 5/15 @ 4:00 PM | Varsity Softball Game | @ Foran (Milford, CT) | | - |
| Wed 5/16 @ TBA | Varsity Baseball Game | @ Fairfield Prep (Fairfield, CT) | | - |
| Thu 5/17 @ 3:45 PM | JV Baseball Game | vs. Fairfield Prep (Fairfield, CT) | | - |
| Thu 5/17 @ 3:45 PM | JV Softball Game | vs. Career Magnet (New Haven, CT) | | - |
| Fri 5/18 @ 3:45 PM | Varsity Softball Game | vs. Wilbur Cross (New Haven, CT) | | - |
| Fri 5/18 @ 3:45 PM | Varsity Baseball Game | @ Career Magnet (New Haven, CT) | | - |
| Fri 5/18 @ 3:45 PM | JV Softball Game | vs. Wilbur Cross (New Haven, CT) | | - |
| Fri 5/18 @ 3:45 PM | Freshman Baseball Game | @ North Branford (CT) | | - |
| Sat 5/19 @ 10:30 AM | JV Baseball Game | @ Career Magnet (New Haven, CT) | | - |
| Sat 5/19 @ 2:00 PM | JV Baseball Game | @ Sheehan (Wallingford, CT) | | - |
| Sat 5/19 @ 3:45 PM | JV Baseball Game | @ Sheehan (Wallingford, CT) | | - |
| Mon 5/21 @ 3:45 PM | JV Softball Game | vs. Sacred Heart Academy (Hamden, CT) | | - |
| Mon 5/21 @ 3:45 PM | Varsity Softball Game | vs. Sacred Heart Academy (Hamden, CT) | | - |
| Tue 5/22 @ 6:30 PM | Varsity Baseball Game | vs. North Branford (CT) | | - |
| Wed 5/23 @ TBA | JV Baseball Game | @ North Branford (CT) | | - |
| Wed 5/23 @ 3:45 PM | JV Baseball Game | @ North Branford (CT) | | - |
| Thu 5/24 @ 3:45 PM | JV Baseball Game | vs. North Branford (CT) | | - |