 | Shepaug Valley Boys Soccer |
|
| Date | Opponent | H/A | Result |
| Wed., 9/12 | Gilbert | Away | W 6-1 |
| Fri., 9/14 | Housatonic Regional | Home | T 0-0 |
| Wed., 9/19 | Northwestern | Away | L 2-1 |
| Fri., 9/21 | Wamogo | Away | T 1-1 |
| Tue., 9/25 | Thomaston | Home | W 1-0 |
| Mon., 10/1 | Terryville | Away | L 2-0 |
| Tue., 10/2 | Litchfield | Away | W 1-0 |
| Fri., 10/5 | Nonnewaug | Away | W 1-0 |
| Tue., 10/9 | Lewis Mills | Home | W 2-0 |
| Thu., 10/11 | Gilbert | Home | W 6-0 |
| Tue., 10/16 | Housatonic Regional | Away | L 3-0 |
| Mon., 10/22 | Terryville | Home | W 5-2 |
| Wed., 10/24 | Wamogo | Home | W 3-0 |
| Fri., 10/26 | Thomaston | Away | W 2-0 |
| Sat., 10/27 | Northwestern | Home | W 1-0 |
| Thu., 11/1 | Nonnewaug | Home | L 1-0 |
 Class S State Tourney |
| Date | [Rd] Opponent | Site | Result |
| Fri., 11/9 | [1st] Lyman Mem. | WCSU | W 1-0 |
| Sat., 11/10 | [2nd] NW Catholic | Shepaug | L 3-1 |