| Squirt IV | ||||
| Date | Time | Location | Opponent | Score |
| September 30-October 9: 2000 Mayor's Cup Tournament | ||||
| 10/8 | 5:00 pm | Neponset | @ Waltham VI | 3-3 |
| 10/14 | 7:00 am | Waltham | TriCounty III | 4-1 |
| 10/21 | 12:00 pm | Somerville | @ Somerville II | 3-7 |
| 10/28 | 9:00 am | South Boston | Quincy C | 1-7 |
| 10/29 | 7:00 am | Somerville | @ Charlestown III | 4-2 |
| 11/5 | 12:00 pm | Neponset | @ Dorchester-Red | (Cancelled) |
| 11/11 | 3:00 pm | Quincy-Shea | Wellesley McNamara | 0-4 |
| 11/18 | 8:00 am | West Roxbury | Belmont III | 1-0 |
| 11/19 | 5:00 pm | Hyde Park | Dedham II | 0-7 |
| 11/25 | 9:00 am | West Roxbury | @ Brookline II | 3-6 |
| 12/2 | 8:10 am | West Roxbury | Brookline III | 4-1 |
| 12/3 | 2:20 pm | Quincy | Dedham II | |
| 12/9 | 8:10 am | Waltham | @ Waltham VI | |
| 12/16 | 11:00 am | Somerville | TriCounty III | |
| 12/23 | 7:00 am | West Roxbury | @ Somerville II | |
| 12/30 | 7:00 am | West Roxbury | Wellesley McNamara | |
| 1/6 | 3:10 pm | Neponset | @ Dorchester-Red | |
| 1/20 | 7:00 am | West Roxbury | Hyde Park B | |
| 1/21 | 6:20 pm | Hyde Park | Belmont III | |
| 1/28 | 6:40 pm | Quincy | @ Brookline II | |
| 2/4 | 6:20 pm | Hyde Park | Brookline III | |
| 2/11 | 8:10 am | Somerville | @ Charlestown III | |
| 2/17 | 7:00 am | West Roxbury | Framingham White | |
| February 19-22: District 1 State Tournament Playdowns | ||||
| 2/24 | 7:00 am | West Roxbury | Waltham VI | 4-2 |
| 3/3 | 8:10 am | West Roxbury | @ TriCounty III | |