| Squirt III | ||||
| Date | Time | Location | Opponent | Score |
| September 30-October 9: 2000 Mayor's Cup Tournament | ||||
| 10/7 | 7:00 am | Waltham | @ Wellesley Stranberg | 1-2 |
| 10/14 | 7:00 am | West Roxbury | Waltham V | 2-0 |
| 10/21 | 2:00 pm | Somerville | TriBoro II | 0-7 |
| 10/22 | 11:00 am | Cleveland Circle | @ TriCounty II | 0-5 |
| 10/28 | 7:00 am | West Roxbury | Charlestown II | 5-2 |
| 11/4 | 10:00 am | South Boston | @ South Boston C | 3-3 |
| 11/11 | 7:00 am | West Roxbury | Needham B2 | 0-1 |
| 11/12 | 1:00 pm | Neponset | @ Dorchester-White | 2-5 |
| 11/25 | 8:00 am | West Roxbury | Allston Brighton I | 2-0 |
| 12/2 | 8:10 am | BU | @ Belmont II | 5-5 |
| 12/3 | 1:20 pm | Quincy | Framingham White | 2-1 |
| 12/10 | 5:10 pm | Hyde Park | @ Wellesley Stranberg | 2-3 |
| 12/16 | 8:10 am | West Roxbury | South Boston C | 1-6 |
| 12/23 | 4:00 pm | Hyde Park | @ Framingham White | 7-1 |
| 1/7 | 2:00 pm | Quincy | @ Waltham V | 3-6 |
| 1/13 | 8:10 am | West Roxbury | Quincy C | 3-6 |
| 1/20 | 10:30 am | Hyde Park | @ Needham B2 | 1-4 |
| 1/21 | 5:10 pm | Hyde Park | Somerville II | 2-3 |
| 1/28 | 10:20 am | Cleveland Circle | @ Allston Brighton I | 4-0 |
| 2/4 | 4:00 pm | Neponset | Belmont II | 1-2 |
| 2/10 | 8:10 am | Charlestown | @ Charlestown II | 3-3 |
| 2/17 | 8:10 am | Hyde Park | Dorchester-White | 3-5 |
| February 19-22: District 1 State Tournament Playdowns | ||||
| 2/24 | 8:10 am | West Roxbury | Wellesley Stranberg | 5-4 |
| 3/3 | 10:30 am | South Boston | @ South Boston C | 2-1 |