| Tue 5/1 @ 3:45 PM | JV Baseball Game | @ Seymour (CT) | | - |
| Wed 5/2 @ TBA | Varsity Baseball Game | vs. Woodland Regional (Beacon Falls, CT) | | - |
| Wed 5/2 @ 3:30 PM | JV Softball Game | @ Woodland Regional (Beacon Falls, CT) | | - |
| Wed 5/2 @ 3:30 PM | Freshman Baseball Game | vs. Woodland Regional (Beacon Falls, CT) | | - |
| Wed 5/2 @ 3:30 PM | Varsity Softball Game | @ Woodland Regional (Beacon Falls, CT)* | | - |
| Thu 5/3 @ TBA | Varsity Baseball Game | @ Kennedy (Waterbury, CT)* | | - |
| Thu 5/3 @ TBA | Varsity Softball Game | vs. Kennedy (Waterbury, CT)* | | - |
| Thu 5/3 @ 3:30 PM | JV Baseball Game | vs. Woodland Regional (Beacon Falls, CT) | | - |
| Thu 5/3 @ 3:30 PM | JV Softball Game | vs. Kennedy (Waterbury, CT) | | - |
| Thu 5/3 @ 3:30 PM | Varsity Softball Game | vs. Kennedy (Waterbury, CT)* | | - |
| Thu 5/3 @ 4:00 PM | Varsity Softball Game | vs. Kennedy (Waterbury, CT)* | | - |
| Fri 5/4 @ 3:30 PM | Freshman Baseball Game | @ Kennedy (Waterbury, CT) | | - |
| Sat 5/5 @ 10:00 AM | JV Baseball Game | @ Kennedy (Waterbury, CT) | | - |
| Mon 5/7 @ TBA | Varsity Softball Game | @ Crosby (Waterbury, CT)* | | - |
| Mon 5/7 @ 3:30 PM | Freshman Baseball Game | vs. Crosby (Waterbury, CT) | | - |
| Mon 5/7 @ 7:00 PM | Varsity Baseball Game | vs. Crosby (Waterbury, CT)* | | - |
| Tue 5/8 @ TBA | Varsity Softball Game | @ Kaynor RVT (Waterbury, CT) | | - |
| Tue 5/8 @ TBA | Varsity Baseball Game | vs. Kaynor RVT (Waterbury, CT) | | - |
| Tue 5/8 @ 3:30 PM | JV Baseball Game | vs. Crosby (Waterbury, CT) | | - |
| Tue 5/8 @ 3:30 PM | Varsity Softball Game | @ Kaynor Tech (Waterbury, CT) | | - |
| Thu 5/10 @ 5:00 PM | JV Softball Game | vs. Naugatuck (CT) | | - |
| Fri 5/11 @ TBA | Varsity Softball Game | vs. Sacred Heart (Waterbury, CT)* | | - |
| Fri 5/11 @ TBA | Varsity Baseball Game | @ Sacred Heart (Waterbury, CT)* | | - |
| Fri 5/11 @ 3:30 PM | Freshman Baseball Game | @ Sacred Heart (Waterbury, CT) | | - |
| Fri 5/11 @ 3:30 PM | JV Softball Game | vs. Convent of the Sacred Heart (Greenwich, CT) | | - |
| Fri 5/11 @ 3:30 PM | Varsity Baseball Game | @ Sacred Heart (Waterbury, CT)* | | - |
| Sat 5/12 @ 10:30 AM | JV Baseball Game | @ Sacred Heart (Waterbury, CT) | | - |
| Sat 5/12 @ 3:30 PM | JV Baseball Game | @ Sacred Heart (Waterbury, CT) | | - |
| Mon 5/14 @ TBA | Varsity Baseball Game | vs. Naugatuck (CT)* | | - |
| Mon 5/14 @ TBA | Varsity Softball Game | @ Naugatuck (CT)* | | - |
| Mon 5/14 @ 3:00 PM | Varsity Softball Game | @ Naugatuck (CT)* | | - |
| Mon 5/14 @ 3:30 PM | JV Softball Game | @ Naugatuck (CT) | | - |
| Mon 5/14 @ 3:30 PM | Freshman Baseball Game | vs. Naugatuck (CT) | | - |
| Mon 5/14 @ 6:00 PM | Varsity Softball Game | @ Naugatuck (CT)* | | - |
| Tue 5/15 @ TBA | Varsity Softball Game | @ Torrington (CT)* | | - |
| Tue 5/15 @ 3:30 PM | JV Baseball Game | vs. Naugatuck (CT) | | - |
| Tue 5/15 @ 3:30 PM | Freshman Baseball Game | vs. Prince RVT (Hartford, CT) | | - |
| Tue 5/15 @ 7:00 PM | Varsity Baseball Game | vs. Torrington (CT)* | | - |
| Wed 5/16 @ TBA | Varsity Baseball Game | vs. Torrington (CT)* | | - |
| Wed 5/16 @ 3:30 PM | JV Baseball Game | vs. Prince RVT (Hartford, CT) | | - |
| Thu 5/17 @ TBA | Varsity Softball Game | vs. Holy Cross (Waterbury, CT)* | | - |
| Thu 5/17 @ 3:30 PM | JV Softball Game | vs. Holy Cross (Waterbury, CT) | | - |
| Thu 5/17 @ 3:30 PM | Varsity Baseball Game | @ Holy Cross (Waterbury, CT)* | | - |
| Thu 5/17 @ 3:30 PM | Varsity Softball Game | vs. Holy Cross (Waterbury, CT)* | | - |
| Thu 5/17 @ 3:30 PM | Freshman Baseball Game | @ Holy Cross (Waterbury, CT) | | - |
| Fri 5/18 @ 3:30 PM | JV Baseball Game | @ Holy Cross (Waterbury, CT) | | - |