| Tue 5/1 @ 3:45 PM | JV Baseball Game | vs. Notre Dame (West Haven, CT) | | - |
| Tue 5/1 @ 4:00 PM | Varsity Girls Lacrosse Game | vs. Branford (CT)* | | - |
| Wed 5/2 @ 3:45 PM | Varsity Softball Game | @ Shelton (CT)* | | - |
| Wed 5/2 @ 3:45 PM | Varsity Baseball Game | vs. Sheehan (Wallingford, CT)* | | - |
| Thu 5/3 @ 3:45 PM | JV Baseball Game | @ Sheehan (Wallingford, CT) | | - |
| Thu 5/3 @ 7:00 PM | Varsity Girls Lacrosse Game | @ Cheshire (CT)* | | - |
| Fri 5/4 @ 3:45 PM | Varsity Softball Game | vs. Lyman Hall (Wallingford, CT)* | | - |
| Fri 5/4 @ 3:45 PM | Freshman Baseball Game | @ Lyman Hall (Wallingford, CT) | | - |
| Fri 5/4 @ 3:45 PM | JV Softball Game | vs. Lyman Hall (Wallingford, CT) | | - |
| Sat 5/5 @ 10:30 AM | JV Baseball Game | vs. Lyman Hall (Wallingford, CT) | | - |
| Sat 5/5 @ 10:30 AM | JV Softball Game | vs. Foran (Milford, CT) | | - |
| Sat 5/5 @ 12:00 PM | JV Softball Game | vs. Foran (Milford, CT) | | - |
| Sat 5/5 @ 1:30 PM | Freshman Baseball Game | vs. Sheehan (Wallingford, CT) | | - |
| Mon 5/7 @ TBA | Varsity Baseball Game | @ Shelton (CT)* | | - |
| Mon 5/7 @ 3:45 PM | JV Baseball Game | vs. Notre Dame (West Haven, CT) | | - |
| Mon 5/7 @ 3:45 PM | JV Softball Game | @ North Haven (CT) | | - |
| Mon 5/7 @ 7:00 PM | Varsity Softball Game | @ North Haven (CT) | | - |
| Tue 5/8 @ TBA | Varsity Baseball Game | @ Lyman Hall (Wallingford, CT)* | | - |
| Tue 5/8 @ 3:45 PM | Freshman Baseball Game | @ Lyman Hall (Wallingford, CT) | | - |
| Tue 5/8 @ 4:00 PM | Varsity Girls Lacrosse Game | vs. North Haven (CT)* | | - |
| Wed 5/9 @ TBA | Freshman Baseball Game | vs. Branford (CT) | | - |
| Wed 5/9 @ 6:30 PM | Varsity Softball Game | vs. Sheehan (Wallingford, CT)* | | - |
| Thu 5/10 @ TBA | JV Baseball Game | @ Branford (CT) | | - |
| Thu 5/10 @ 3:45 PM | JV Baseball Game | @ Branford (CT) | | - |
| Thu 5/10 @ 3:45 PM | JV Softball Game | vs. East Haven (CT) | | - |
| Thu 5/10 @ 3:45 PM | Freshman Baseball Game | @ Lyman Hall (Wallingford, CT) | | - |
| Thu 5/10 @ 4:00 PM | JV Baseball Game | @ Branford (CT) | | - |
| Thu 5/10 @ 4:00 PM | Varsity Girls Lacrosse Game | vs. Guilford (CT)* | | - |
| Fri 5/11 @ TBA | Varsity Softball Game | vs. Cheshire (CT)* | | - |
| Fri 5/11 @ 3:45 PM | Varsity Baseball Game | vs. Cheshire (CT)* | | - |
| Fri 5/11 @ 3:45 PM | JV Softball Game | vs. Cheshire (CT) | | - |
| Fri 5/11 @ 3:45 PM | Freshman Baseball Game | vs. Cheshire (CT) | | - |
| Sat 5/12 @ TBA | Varsity Baseball Game | vs. Branford (CT) | | - |
| Sat 5/12 @ 10:30 AM | JV Softball Game | vs. Hand (Madison, CT) | | - |
| Sat 5/12 @ 12:00 PM | JV Softball Game | vs. Hand (Madison, CT) | | - |
| Sat 5/12 @ 12:30 PM | JV Baseball Game | @ Cheshire (CT) | | - |
| Mon 5/14 @ TBA | Varsity Softball Game | @ Hand (Madison, CT)* | | - |
| Mon 5/14 @ TBA | Varsity Baseball Game | vs. Hand (Madison, CT) | | - |
| Mon 5/14 @ TBA | Varsity Boys Volleyball Game | @ Xavier (Middletown, CT)* | | - |
| Mon 5/14 @ 3:45 PM | Freshman Baseball Game | vs. Hand (Madison, CT) | | - |
| Mon 5/14 @ 3:45 PM | JV Softball Game | @ Hand (Madison, CT) | | - |
| Mon 5/14 @ 4:00 PM | Varsity Lacrosse Game | @ Wilbur Cross (New Haven, CT)* | | - |
| Tue 5/15 @ 3:45 PM | JV Baseball Game | @ Hand (Madison, CT) | | - |
| Wed 5/16 @ TBA | Varsity Baseball Game | @ Xavier (Middletown, CT) | | - |
| Wed 5/16 @ 3:45 PM | Freshman Baseball Game | @ Xavier (Middletown, CT) | | - |
| Wed 5/16 @ 3:45 PM | JV Softball Game | vs. Hamden (CT) | | - |
| Wed 5/16 @ 6:30 PM | Varsity Softball Game | vs. Hamden (CT) | | - |
| Thu 5/17 @ 3:45 PM | JV Baseball Game | vs. Xavier (Middletown, CT) | | - |
| Thu 5/17 @ 4:00 PM | Varsity Girls Lacrosse Game | @ Sacred Heart Academy (Hamden, CT)* | | - |
| Thu 5/17 @ 6:00 PM | Varsity Lacrosse Game | vs. Shelton (CT)* | | - |
| Fri 5/18 @ 3:45 PM | JV Softball Game | @ West Haven (CT) | | - |
| Fri 5/18 @ 3:45 PM | Freshman Baseball Game | @ North Haven (CT) | | - |
| Fri 5/18 @ 7:00 PM | Varsity Softball Game | @ West Haven (CT) | | - |
| Fri 5/18 @ 7:00 PM | Varsity Baseball Game | @ North Haven (CT) | | - |
| Sat 5/19 @ 10:30 AM | JV Baseball Game | vs. North Haven (CT) | | - |
| Sat 5/19 @ 12:00 PM | Varsity Girls Lacrosse Game | @ West Haven (CT)* | | - |
| Sat 5/19 @ 12:30 PM | Freshman Baseball Game | @ Xavier (Middletown, CT) | | - |
| Mon 5/21 @ 4:00 PM | Varsity Girls Lacrosse Game | @ Guilford (CT)** | | - |
| Wed 5/23 @ 3:30 PM | Varsity Baseball Game | @ Foran (Milford, CT)** | | - |
| Thu 5/24 @ 7:00 PM | Varsity Baseball Game | vs. Hand (Madison, CT)** | | - |
| Sat 5/26 @ 12:00 PM | Varsity Baseball Game | @ Shelton (CT)** | | - |
| Sat 5/26 @ 6:00 PM | Varsity Softball Game | @ Foran (Milford, CT)** | | - |
| Tue 5/29 @ 3:30 PM | Varsity Baseball Game | @ Ludlowe (Fairfield, CT)*** | | - |
| Wed 5/30 @ 3:30 PM | Varsity Baseball Game | vs. Xavier (Middletown, CT) | | - |