| Wed 5/2 @ TBA | Varsity Softball Game | @ Wamogo Regional (Litchfield, CT)* | | - |
| Wed 5/2 @ 3:45 PM | Varsity Baseball Game | vs. Wamogo Regional (Litchfield, CT)* | | - |
| Fri 5/4 @ 3:45 PM | Varsity Baseball Game | @ Wolcott RVT (Torrington, CT) | | - |
| Fri 5/4 @ 7:00 PM | Varsity Softball Game | @ Wolcott (CT) | | - |
| Mon 5/7 @ 3:45 PM | Varsity Softball Game | @ Housatonic (Falls Village, CT)* | | - |
| Mon 5/7 @ 3:45 PM | Varsity Baseball Game | vs. Housatonic (Falls Village, CT)* | | - |
| Mon 5/7 @ 3:50 PM | Varsity Softball Game | @ Housatonic-Wamogo (Falls Village, CT) | | - |
| Mon 5/7 @ 3:55 PM | JV Softball Game | @ Housatonic-Wamogo (Falls Village, CT) | | - |
| Wed 5/9 @ TBA | Varsity Baseball Game | vs. Northwestern Regional (Winsted, CT)* | | - |
| Mon 5/14 @ 3:45 PM | Varsity Baseball Game | vs. Nonnewaug (Woodbury, CT)* | | - |
| Tue 5/15 @ TBA | Varsity Softball Game | vs. Northwestern Regional (Winsted, CT)* | | - |
| Wed 5/16 @ TBA | Varsity Baseball Game | vs. Thomaston (CT)* | | - |
| Wed 5/16 @ TBA | Varsity Softball Game | @ Thomaston (CT)* | | - |
| Thu 5/17 @ 3:45 PM | Varsity Softball Game | @ Nonnewaug (Woodbury, CT)* | | - |
| Fri 5/18 @ TBA | Varsity Softball Game | vs. Litchfield (CT)* | | - |
| Fri 5/18 @ 3:45 PM | Varsity Baseball Game | @ Litchfield (CT)* | | - |
| Mon 5/21 @ TBA | Varsity Softball Game | @ Gilbert (Winsted, CT)* | | - |
| Mon 5/21 @ 3:45 PM | Varsity Baseball Game | vs. Gilbert (Winsted, CT)* | | - |
| Tue 5/22 @ 3:45 PM | Varsity Baseball Game | vs. Wolcott RVT (Torrington, CT) | | - |
| Wed 5/23 @ TBA | Varsity Baseball Game | @ Lewis Mills (Burlington, CT)*** | | - |
| Wed 5/23 @ TBA | Varsity Softball Game | vs. Lewis Mills (Burlington, CT)* | | - |
| Wed 5/23 @ 3:45 PM | JV Softball Game | vs. Lewis Mills (Burlington, CT) | | - |
| Thu 5/24 @ TBA | Varsity Baseball Game | @ Wolcott (CT)*** | | - |
| Tue 5/29 @ 3:30 PM | Varsity Baseball Game | @ Coginchaug Regional (Durham, CT)*** | | - |