- Winchendon School Varsity Hockey, 1999-00
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- Sat. 11/27 @Cushing Academy 6:00
- Sat. 12/4 @Hebron Academy 7:00
- Sun. 12/5 @Bridgton Academy 1:00
- Wed. 12/8 @Phillips Exeter Academy 3:30
- Sat. -Sun. 12/11-12/12 @Albany Academy Tournament
- Wed. 12/15 Pomfret 3:10
- Fri.-Sat. 12/17-12/18 @ Barber Tournament
- Mon.-Wed. 12/28-12/30 BB&N Tournament
- Sat. 1/8 Hebron Academy 4:20
- Sun. 1/9 National Sports Academy 11:00 am
- Wed. 1/12 @Holderness School 4:00
- Sat. 1/15 Lawrenceville School 8:00
- Sun. 1/16 Hill School 10:00 am
- Wed. 1/19 @Pomfret 4:00
- Fri. 1/21 Northfield Mt. Hermon 3:10
- Tues. 1/25 New Hampton 3:10
- Wed. 1/26 @Gunnery 5:00
- Sat. 1/29 @Berkshire School 2:00
- Sun. 1/30 @Canterbury School 1:00
- Wed. 2/2 @Tilton School 4:00
- Sat. 2/5 Albany Academy 2:50
- Wed. 2/9 @Cushing Academy 5:30
- Sat. 2/12 Berkshire School 4:20
- Wed. 2/16 Gunnery School 3:10
- Sat. 2/19 @Lawrenceville 7:00
- Sun. 2/20 @Hill School 1:00
- Wed. 2/23 @Vermont Academy 3:00
- Sat. 2/26 Bridgton Academy 3:10