| PeeWee III | ||||
| Date | Time | Location | Opponent | Score |
| 9/23 | 7:00 am | Hyde Park | Charlestown II | 1-0 |
| September 30-October 9: 2000 Mayor's Cup Tournament | ||||
| 10/7 | 7:00 am | Hyde Park | @ Dedham II | 3-0 |
| 10/21 | 6:00 pm | Hyde Park | Dorchester-Red | 2-5 |
| 10/22 | 9:00 am | Charlestown | Allston-Brighton I | 0-0 |
| 10/28 | 9:00 am | West Roxbury | TriBoro II | 0-5 |
| 11/4 | 5:00 pm | Hyde Park | @ Waltham III | 1-1 |
| 11/11 | 7:00 pm | St. Sebastians | @ TriCounty AB | 2-4 |
| 11/18 | 6:00 pm | Hyde Park | Quincy B | 1-5 |
| 11/25 | 5:00 pm | Hyde Park | Framingham Blue | |
| 11/26 | 4:00 pm | Hyde Park | Belmont III | |
| 12/3 | 3:30 pm | Neponset | @ South Boston C | 0-0 |
| 12/9 | 6:20 pm | Cleveland Circle | @ Needham B3 | 4-4 |
| 12/16 | 6:20 pm | Hyde Park | South Boston C | 2-3 |
| 12/23 | 7:30 pm | Hyde Park | @ Framingham Blue | 2-8 |
| 12/30 | 5:30 pm | Neponset | @ Dorchester-White | 0-5 |
| 1/7 | 4:00 pm | Hyde Park | @ Quincy C | 2-2 |
| 1/14 | 4:00 pm | Hyde Park | Somerville II | 4-4 |
| 1/20 | 5:10 pm | Hyde Park | Hyde Park B | 5-5 |
| 1/27 | 5:40 pm | St. Sebastians | @ Allston Brighton I | 2-7 |
| 2/3 | 8:40 pm | Hyde Park | Framingham C | |
| 2/10 | 4:00 pm | Hyde Park | @ Dedham II | |
| 2/17 | 7:30 pm | Hyde Park | Dorchester-Red | |
| February 19-22: District 1 State Tournament Playdowns | ||||
| 2/24 | 6:20 pm | Hyde Park | Waltham III | |
| 3/4 | 11:00 am | South Boston | @ South Boston C | |