Winchester boys soccer
Conference: Middlesex
| Date | Opponent | Time/result |
| Thu., Sept. 4 | at Burlington | W, 5-1 |
| Sat., Sept. 6 | at Reading | W, 4-0 |
| Thu., Sept. 18 | Wakefield | W, 5-1 |
| Mon., Sept. 22 | Melrose | W, 4-1 |
| Thu., Sept. 25 | at Watertown | W, 4-1 |
| Mon., Sept. 29 | at Woburn | T, 1-1 |
| Tue., Oct. 7 | Reading | W, 4-2 |
| Sat., Oct. 11 | at Stoneham | L, 1-0 |
| Mon., Oct. 13 | Lexington | L, 1-0 |
| Tue., Oct. 21 | at Wakefield | W, 3-0 |
| Sat., Oct. 25 | Melrose | W, 5-0 |
| Sat., Nov. 1 | Woburn | W, 3-1 |
| Sat., Nov. 8 | at Dracut | W, 4-3 |
| Tue., Nov. 11 | Wayland | W, 4-0 |
| Thu., Nov. 13 | Bedford | W, 1-0 |
| Sun., Nov. 16 | Masconomet | L, 2-0 |
Schedules subject to change. To report a correction or an update, please notify the Globe sports department.
Updated: Friday, Dec. 19, 2008, 10:10 p.m.
Schedules and results