| Terryville Varsity Boys Golf |
| Northwestern, Gilbert (V) Terryville 270 Mon. 9/12, 3:00 - Away - Northwestern Regional H.S.-Norfolk CC |
| Wamogo, Housatonic Regional (V) Mon. 9/19, 3:00 - Away - Wamogo High School-Stoneybrook Golf Course Driving Directions |
| Nonnewaug, Gilbert (V) Terryville 268 Tue. 9/20, 3:00 - Away - Crestbrook Park-Crestbrook Park Golf |
| Housatonic Regional (V) Terryville 274 Tue. 9/27, 3:00 - Home - Pequabuck Golf Club-Golf Course, Front 9 |
| Shepaug Valley (V) Terryville 260 Thu. 10/6, 3:00 - Away - Washington Club Golf Course |
| Litchfield (V) Terryville 296 Tue. 10/11, 3:00 - Away - Litchfield Country Club |
| Nonnewaug, Shepaug Valley (V) Terryville 270 Wed. 10/12, 3:00 - Home - Pequabuck Golf Club-Golf Course, Front 9 |
| Litchfield, Northwestern, Wamogo (V) Thu. 10/13, 3:00 - Home - Pequabuck Golf Club-Golf Course, Front 9 Driving Directions |
| BL Golf All Star Tournament (V) Tue. 10/18, 8:00 - Away - Fairfiew Farm Golf Course |
| CIAC Division II Championship (V) Mon. 10/24, 8:30 - Away - Chippanee GC |