| PeeWee IV | ||||
| Date | Time | Location | Opponent | Score |
| September 30-October 9: 2000 Mayor's Cup Tournament | ||||
| 10/14 | 1:00 pm | Neponset | Framingham White | |
| 10/15 | 4:30 pm | Quincy | @ Quincy C | |
| 10/21 | 3:00 pm | St. Sebastians | Hyde Park C | |
| 10/22 | 6:00 pm | Hyde Park | @ Needham B3 | |
| 10/29 | 3:25 pm | St. Sebastians | Dedham III | |
| 11/5 | 4:00 pm | Hyde Park | Wellesley Testa | |
| 11/11 | 5:10 pm | Cleveland Circle | @ Brookline II | |
| 11/18 | 9:00 am | West Roxbury | Quincy C | |
| 11/19 | 2:15 pm | St. Sebastians | @ Framingham White | |
| 11/25 | 7:00 pm | Hyde Park | Hyde Park C | |
| 12/2 | 6:20 pm | Hyde Park | @ Hyde Park C | |
| 12/3 | 4:00 pm | Hyde Park | @ Wellesley Testa | |
| 12/9 | 10:30 am | Hyde Park | Hyde Park C | |
| 12/16 | 5:10 pm | Hyde Park | Belmont III | |
| 12/17 | 10:20 am | Cleveland Circle | @ Wellesley Testa | |
| 12/23 | 8:40 pm | Cleveland Circle | @ Brookline II | |
| 12/30 | 3:10 pm | Neponset | @ Waltham III | |
| 1/7 | 10:30 am | Somerville | Dedham III | |
| 1/14 | 9:40 am | Loring | @ Framingham White | |
| 1/20 | 7:30 pm | Cleveland Circle | @ Wellesley Testa | |
| 1/27 | 7:00 am | Waltham | @ Wellesley Testa | |
| 2/4 | 3:10 pm | Quincy | @ Belmont III | |
| 2/11 | 2:15 pm | St. Sebastians | Brookline II | |
| 2/17 | 5:10 pm | Hyde Park | Needham B3 | |
| February 19-22: District 1 State Tournament Playdowns | ||||
| 2/24 | 5:10 pm | Cleveland Circle | @ Dedham III | |
| 3/4 | 4:00 pm | Hyde Park | Framingham White | |