| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| THU 9/9 | 5:45 p.m. | Varsity | League | Normal | Away | Bethel | Loss | 0-3 | | Bethel High School-BHS gym | |
| SAT 9/11 | 12:00 p.m. | Varsity | League | Normal | Home | WamogoReg | Win | 3-0 | | New Fairfield High School-High School Gym | |
| FRI 9/17 | 6:15 p.m. | Varsity | League | Normal | Home | HousatonicValleyReg | Loss | 2-3 | | New Fairfield High School-High School Gym | |
| SAT 9/18 | 12:00 p.m. | Varsity | League | Normal | Away | WamogoReg | Win | 3-0 | | Wamogo Regional High School-Large gym | |
| MON 9/20 | 6:15 p.m. | Varsity | League | Normal | Away | NotreDameCatholic | Win | 3-1 | | Notre Dame - Fairfield -Sister Marion Reilly Auditorium | |
| WED 9/22 | 7:00 p.m. | Varsity | League | Normal | Home | Newtown | Loss | 0-3 | | New Fairfield High School-High School Gym | |
| FRI 9/24 | 7:00 p.m. | Varsity | League | Normal | Away | Immaculate | Loss | 0-3 | | Immaculate High School-Immaculate Gym | |
| MON 9/27 | 5:30 p.m. | Varsity | League | Normal | Home | Bunnell | Loss | 1-3 | | New Fairfield High School-High School Gym | |
| WED 9/29 | 6:00 p.m. | Varsity | League | Normal | Away | JoelBarlow | Loss | 03 | | Joel Barlow High School-Lower Gym | |
| FRI 10/1 | 6:45 p.m. | Varsity | League | Normal | Home | NewMilford | Loss | 0-3 | | New Fairfield High School-High School Gym | |
| MON 10/4 | 5:30 p.m. | Varsity | League | Normal | Home | Stratford | Loss | 0-3 | | New Fairfield High School-High School Gym | |
| WED 10/6 | 6:15 p.m. | Varsity | League | Normal | Away | Masuk | Loss | 0-3 | | Masuk High School-David Strong Gymnasium @ Masuk HS | |
| FRI 10/8 | 5:30 p.m. | Varsity | League | Normal | Away | Weston | Loss | 0-3 | | Weston High School-Gym (New) | |
| TUE 10/12 | 6:00 p.m. | Varsity | League | Normal | Away | Bunnell | Loss | 2-3 | | Bunnell HS-David Johnson Gymnasium | |
| THU 10/14 | 7:00 p.m. | Varsity | League | Normal | Home | Pomperaug | Loss | 0-3 | | New Fairfield High School-High School Gym | |
| SAT 10/16 | 9:00 a.m. | Varsity | League | Normal | Away | Brookfield | Loss | 0-3 | | Brookfield High School-BHS Big Gym | |
| TUE 10/19 | 5:30 p.m. | Varsity | League | Normal | Home | Bethel | Loss | 0-3 | | New Fairfield High School-High School Gym | |
| WED 10/20 | 6:00 p.m. | Varsity | League | Normal | Away | KolbeCathedral | Loss | 1-3 | | Kolbe Cathedral High School-Gym | |
| MON 10/25 | 5:30 p.m. | Varsity | League | Normal | Home | NotreDameCatholic | Loss | 1-3 | | New Fairfield High School-High School Gym | |
| WED 10/27 | 5:30 p.m. | Varsity | League | Normal | Home | HenryAbbottRVT | Win | 3-1 | | New Fairfield High School-High School Gym | |