| PeeWee I | ||||
| Date | Time | Location | Opponent | Score |
| September 30-October 9: 2000 Mayor's Cup Tournament | ||||
| 9/23 | 11:00 am | BU | Charlestown I | |
| 10/7 | 10:00 am | South Boston | TriBoro I | |
| 10/14 | 7:00 pm | St. Sebastians | @ Needham A | 1-0 (Forfeit) |
| 10/21 | 8:00 pm | St. Sebastians | @ Charlestown I | |
| 10/28 | 7:00 pm | Hyde Park | @ Belmont I | |
| 11/4 | 8:00 pm | Hyde Park | South Boston A | |
| 11/11 | 9:00 am | West Roxbury | South Boston B | 6-1 |
| 11/12 | 7:00 am | Loring | @ Framingham A | |
| 11/18 | 8:00 pm | Hyde Park | Wellesley Covo | |
| 11/25 | 9:00 pm | Hyde Park | Dorchester I | |
| 12/2 | 8:40 pm | Hyde Park | Hyde Park A | |
| 12/9 | 8:40 pm | Hyde Park | Charlestown I | |
| 12/16 | 5:30 pm | Neponset | @ Dorchester I | |
| 12/23 | 8:00 pm | St. Sebastians | Wellesley Covo | |
| 12/30 | 8:40 pm | Hyde Park | @ Hyde Park A | |
| 1/6 | 8:40 pm | Hyde Park | Belmont I | |
| 1/13 | 7:30 pm | Hyde Park | @ South Boston B | |
| 1/27 | 5:10 pm | Hyde Park | @ South Boston A | |
| 1/28 | 9:20 am | Somerville | @ Wellesley Covo | |
| 2/3 | 6:20 pm | Hyde Park | @ TriBoro I | |
| 2/10 | 8:40 pm | Hyde Park | Dedham I | |
| 2/18 | 11:40 am | Quincy | Needham A | |
| February 19-22: District 1 State Tournament Playdowns | ||||
| 2/24 | 7:30 pm | Hyde Park | Waltham I | |
| 3/3 | 5:10 pm | Hyde Park | @ Quincy A | |