| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| MON 4/3 | 4:15 p.m. | Varsity | League | Normal | Home | Weston | Loss | 10-8 | | Joel Barlow High-Field E (Softball) | |
| TUE 4/4 | 4:15 p.m. | Varsity | League | Normal | Home | Stratford | Loss | 31-7 | | Joel Barlow High-Field E (Softball) | |
| THU 4/6 | 3:45 p.m. | Varsity | League | Normal | Away | Bunnell | Loss | 24-1 | | Bunnell HS-Bunnell Softball FIeld | |
| MON 4/10 | 4:15 p.m. | Varsity | League | Normal | Away | NewFairfield | Loss | 18-4 | | New Fairfield High School-Softball Field | |
| WED 4/12 | 4:15 p.m. | Varsity | League | Normal | Home | KolbeCathedral | Loss | 13-4 | | Joel Barlow High-Field E (Softball) | |
| FRI 4/14 | 11:00 a.m. | Varsity | League | Normal | Home | WarrenHarding | Win | 13-3 | | Joel Barlow High-Field E (Softball) | |
| MON 4/17 | 4:15 p.m. | Varsity | League | Normal | Home | Immaculate | Loss | 18-1 | | Joel Barlow High-Field E (Softball) | |
| WED 4/19 | 4:15 p.m. | Varsity | League | Normal | Away | Brookfield | Loss | 16-1 | | Brookfield High School-BHS Softball Field | |
| THU 4/20 | 4:15 p.m. | Varsity | League | Normal | Home | Newtown | Loss | 24-0 | | Joel Barlow High-Field E (Softball) | |
| MON 4/24 | 4:15 p.m. | Varsity | League | Normal | Home | Stratford | Loss | 14-0 | | Joel Barlow High-Field E (Softball) | |
| WED 4/26 | 4:15 p.m. | Varsity | League | Normal | Away | NotreDameCatholic | Loss | 20-6 | | Notre Dame - Fairfield -Park Ave Field | |
| FRI 4/28 | 4:15 p.m. | Varsity | League | Normal | Home | NewMilford | Loss | 20-0 | | Joel Barlow High-Field E (Softball) | |
| MON 5/1 | 4:15 p.m. | Varsity | League | Normal | Away | Masuk | Loss | 13-0 | | Masuk High School-Masuk High School Softball Field | |
| WED 5/3 | 4:15 p.m. | Varsity | League | Normal | Home | Bethel | Loss | 17-0 | | Joel Barlow High-Field E (Softball) | |
| MON 5/8 | 4:15 p.m. | Varsity | League | Normal | Home | Bunnell | Loss | 16-3 | | Joel Barlow High-Field E (Softball) | |
| WED 5/10 | 4:30 p.m. | Varsity | League | Normal | Away | Weston | Loss | 14-2 | | Weston High School-Softball - North House Field (Hurlbutt El. School) | |
| FRI 5/12 | 4:30 p.m. | Varsity | League | Normal | Away | WarrenHarding | Win | 19-1 | | Warren Harding High School-Caribe Field- 300 Asylum Street | |
| MON 5/15 | 4:15 p.m. | Varsity | League | Normal | Home | Pomperaug | Loss | 13-0 | | Joel Barlow High-Field E (Softball) | |
| TUE 5/16 | 4:15 p.m. | Varsity | League | Normal | Away | Bethel | Loss | 15-8 | | Bethel High School-Kisling Field | |
| THU 5/18 | 4:15 p.m. | Varsity | League | Normal | Home | HenryAbbottRVT | Win | 16-2 | | Joel Barlow High-Field E (Softball) | |