| Squirt II | ||||
| Date | Time | Location | Opponent | Score |
| September 30-October 9: 2000 Mayor's Cup Tournament | ||||
| 10/7 | 4:00 pm | Neponset | @ Wellesley Clendenen | 1-1 |
| 10/14 | 8:00 am | West Roxbury | Somerville I | 2-1 |
| 10/21 | 7:00 am | South Boston | @ South Boston B | |
| 10/28 | 8:00 am | West Roxbury | Quincy B | 3-3 |
| 11/4 | 11:00 am | Neponset | @ Dorchester II | |
| 11/5 | 1:05 pm | St. Sebastians | @ Needham B1 | |
| 11/11 | 7:00 am | Hyde Park | Waltham II | |
| 11/12 | 9:00 am | Somerville | Hyde Park A | |
| 11/18 | 7:00 am | West Roxbury | Brookline I | |
| 11/25 | 8:00 am | BU | @ Charlestown I | |
| 12/2 | 7:00 am | West Roxbury | Dedham I | |
| 12/3 | 3:20 pm | Quincy | @ Dorchester II | |
| 12/9 | 1:20 pm | Somerville | @ Wellesley Clendenen | 3-3 |
| 12/16 | 7:00 am | West Roxbury | Somerville I | 2-6 |
| 12/23 | 8:10 am | West Roxbury | @ South Boston B | 4-8 |
| 12/30 | 8:10 am | West Roxbury | Hyde Park A | 5-0 |
| 1/6 | 8:10 am | West Roxbury | @ Needham B1 | 2-2 |
| 1/7 | 9:40 am | Loring | South Boston B | 2-2 |
| 1/13 | 7:00 am | West Roxbury | Waltham II | 1-4 |
| 1/20 | 7:00 am | Hyde Park | TriCounty II | 3-0 |
| 1/27 | 10:30 am | South Boston | @ TriBoro II | |
| 2/3 | 7:00 am | West Roxbury | Brookline I | |
| 2/10 | 7:00 am | Neponset | @ Dorchester II | |
| 2/17 | 8:10 am | West Roxbury | Quincy B | |
| 2/25 | 9:20 am | Somerville | Wellesley Clendenen | |
| 3/4 | 7:00 am | Somerville | @ Somerville I | |