| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 12/13 | 5:30 PM | Varsity | League | Normal | Away | Fairfield Prep | | | | Fairfield University - Leo D. Mahoney Arena | 3:30 PM - 1 Bus |
| WED 12/20 | 7:00 PM | Varsity | League | Normal | Home | Amity | | | | Jonathan Law High School - James L. Richetelli Memorial Gymnasium | |
| WED 12/27 | 9:30 PM | Varsity | League | Normal | Away | Middletown | | | | Simsbury High School - Gym 2 | |
| Somers | | |
| Bloomfield Weaver | | |
| East Hartford | | |
| Simsbury | | |
| | |
| Staples | | |
| | |
| | |
| | |
| FRI 12/29 | 9:00 AM | Varsity | League | Normal | Home | New Haven Wrestling | | | | Jonathan Law High School - James L. Richetelli Memorial Gymnasium | |
| North Haven | | |
| Bunnell | | |
| Derby/Oxford/Holy Cross | | |
| Terryville-Thomaston | | |
| Platt | | |
| WED 1/3 | 7:00 PM | Varsity | League | Normal | Away | Notre Dame-West Haven | | | | Notre Dame High School - Gym | 5:15 PM - 1 Bus |
| SAT 1/6 | 9:00 AM | Varsity | Tournament | Normal | Home | East Lyme/Norwich Tech | | | | Jonathan Law High School - James L. Richetelli Memorial Gymnasium | |
| Bethel | | |
| Killingly | | |
| Masuk | | |
| Foran | | |
| St. Joseph | | |
| WED 1/10 | 7:00 PM | Varsity | League | Normal | Home | Cheshire | | | | Jonathan Law High School - James L. Richetelli Memorial Gymnasium | |
| SAT 1/13 | 9:00 AM | Varsity | Tournament | Normal | Away | Waterford | | | | Ellis R V Tech School - Gym | 6:45 AM - 1 Bus |
| Middletown | | |
| Terryville-Thomaston | | |
| Bacon Academy | | |
| East Haven | | |
| Ellis Tech | | |
| North Haven | | |
| WED 1/17 | 7:00 PM | Varsity | League | Normal | Home | Foran | | | | Jonathan Law High School - James L. Richetelli Memorial Gymnasium | |
| SAT 1/20 | 10:00 AM | Varsity | Non-League | Normal | Away | Staples | | | | Norwich Free Academy - Alumni Gym | 7:00 AM - 1 Bus |
| Bristol Central | | |
| Ellis Tech | | |
| Ledyard | | |
| Norwich Free Academy | | |
| | |
| Notre Dame-West Haven | | |
| WED 1/24 | 6:00 PM | Varsity | League | Normal | Away | East Haven | | | | East Haven High School - Gym | 4:00 PM - 1 Bus |
| SAT 1/27 | 9:30 AM | Varsity | Tournament | Normal | Away | Joel Barlow | | | | Brookfield High School - BHS Small & Big Gym | 7:15 AM - 1 Bus |
| Stamford | | |
| Darien | | |
| Wilton | | |
| Shelton | | |
| Danbury | | |
| Masuk | | |
| Westhill | | |
| Brookfield/Shepaug | | |
| New Canaan | | |
| Pomperaug | | |
| Derby/Oxford/Holy Cross | | |
| St. Joseph | | |
| WED 1/31 | 6:00 PM | Varsity | League | Normal | Away | New Haven Wrestling | | | | Wilbur Cross High School - Little Gym | 4:15 PM - 1 Bus |
| SAT 2/3 | 9:00 AM | Varsity | Non-League | Normal | Away | Foran | | | | Foran High School - Edna L. Fraser Gymnasium | 7:30 AM - 1 Bus |
| Darien | | |
| Amity | | |
| Stratford | | |
| Bunnell | | |
| WED 2/7 | 7:00 PM | Varsity | League | Normal | Home | Daniel Hand | | | | Jonathan Law High School - James L. Richetelli Memorial Gymnasium | |