| PeeWee II | ||||
| Date | Time | Location | Opponent | Score |
| 9/23 | 9:20 am | Charlestown | Waltham II | 2-0 |
| September 30-October 9: 2000 Mayor's Cup Tournament | ||||
| 10/14 | 7:00 pm | Hyde Park | @ Somerville I | 5-5 |
| 10/15 | 9:00 am | Hyde Park | TriCounty I | 1-0 (Forfeit) |
| 10/21 | 9:00 pm | Hyde Park | Quincy A | 0-6 |
| 10/28 | 9:00 pm | St. Sebastians | @ Needham B1 | 2-0 |
| 11/11 | 8:40 pm | Hyde Park | Belmont II | 2-1 |
| 11/12 | 8:00 am | Hyde Park | Framingham C | 1-0 (Forfeit) |
| 11/18 | 7:00 pm | Hyde Park | @ Brookline I | 3-1 |
| 11/25 | 6:00 pm | Hyde Park | Dedham I | 1-3 |
| 12/2 | 7:30 pm | Hyde Park | @ Framingham B | 6-6 |
| 12/3 | 9:20 am | BU | Waltham II | 3-1 |
| 12/9 | 6:20 pm | Hyde Park | Brookline I | 3-4 |
| 12/16 | 6:50 pm | St. Sebastians | @ Needham B2 | 4-1 |
| 12/23 | 9:20 am | Hyde Park | Framingham B | 3-5 |
| 12/30 | 8:00 pm | Charlestown | @ Charlestown II | 4-3 |
| 1/6 | 6:20 pm | Hyde Park | Needham B1 | 2-1 |
| 1/13 | 8:40 pm | Hyde Park | @ Quincy B | 1-1 |
| 1/20 | 6:20 pm | Hyde Park | @ Belmont II | 2-4 |
| 1/27 | 8:40 pm | Hyde Park | Somerville I | 2-4 |
| 2/3 | 9:10 pm | St. Sebastians | @ Wellesley Crane | 3-2 |
| 2/10 | 7:30 pm | Hyde Park | Waltham II | 5-0 |
| 2/17 | 8:40 pm | Hyde Park | @ TriBoro II | 1-2 |
| February 19-22: District 1 State Tournament Playdowns | ||||
| 2/24 | 5:10 pm | Hyde Park | Wellesley Ballantyne | 5-1 |
| 3/3 | 4:00 pm | Hyde Park | @ TriCounty AB | 5-1 |