| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 9/8 | 3:00 p.m. | Varsity | League | Normal | Away | Litchfield | | | | Litchfield Country Club | |
| THU 9/16 | 3:00 p.m. | Varsity | League | Normal | Home | Litchfield | | | | Western Hills Golf Course (Wtby) | |
| MON 9/20 | 3:00 p.m. | Varsity | League | Normal | Home | NorthwesternReg | | | | Western Hills Golf Course (Wtby) | |
| TUE 9/21 | 3:00 p.m. | Varsity | League | Normal | Away | ShepaugValley | | | | Lake Waramaug Country Club | |
| THU 9/23 | 3:00 p.m. | Varsity | League | Normal | Home | Gilbert | | | | Western Hills Golf Course (Wtby) | |
| MON 9/27 | 3:00 p.m. | Varsity | League | Normal | Home | HousatonicValleyReg | | | | Western Hills Golf Course (Wtby) | |
| WED 9/29 | 3:00 p.m. | Varsity | League | Normal | Away | HousatonicValleyReg | | | | Canaan Country Club | |
| MON 10/4 | 3:00 p.m. | Varsity | League | Normal | Away | Gilbert | | | | Green woods Country Club | |
| TUE 10/5 | 3:00 p.m. | Varsity | League | Normal | Away | ShepaugValley | | | | Lake Waramaug Country Club | |
| WED 10/6 | 3:00 p.m. | Varsity | League | Normal | Home | Gilbert | | | | Western Hills Golf Course (Wtby) | |
| THU 10/7 | 3:30 p.m. | Varsity | League | Normal | Away | NorthwesternReg | | | | Northwestern Regional H.S.-Norfolk CC | |