| PeeWee II | ||||
| Date | Time | Rink | Opponent | Score |
| October 2-11: 1999 Mayor's Cup Tournament | ||||
| 10/9 | 7:30 pm | UMass-Boston | Allston Brighton | 1-0 |
| 10/16 | 7:30 pm | Hyde Park | Brookline B | 2-2 |
| 10/23 | 7:30 pm | Hyde Park | Dorchester II | 7-2 |
| 10/30 | 6:20 pm | Hyde Park | Needham B2 | 3-3 |
| 10/31 | 11:30 am | Belmont High | Belmont II | 5-2 |
| 11/6 | 7:30 pm | Hyde Park | Dedham Open | 4-1 |
| 11/13 | 8:00 pm | Charlestown | Belmont II | 5-4 |
| 11/20 | BYE | |||
| 11/27 | 5:10 pm | Hyde Park | TriCounty B | 3-2 |
| 12/4 | 8:40 pm | Hyde Park | Quincy B | 3-2 |
| 12/5 | 9:10 am | Hyde Park | Waltham B | 2-2 |
| 12/11 | 7:30 pm | Cleveland Circle | Brookline B | 1-2 |
| 12/18 | 5:10 pm | Cleveland Circle | Dorchester II | 4-2 |
| 1/2 | 10:30 am | Charlestown | Charlestown II | 1-1 |
| 1/8 | 6:20 pm | Hyde Park | Dedham Open | 2-0 |
| 1/16 | 5:10 pm | Hyde Park | Framingham C1 | 5-2 |
| 1/22 | 8:00 pm | St. Sebastians | Waltham II | 0-0 |
| 1/29 | 8:40 pm | Cleveland Circle | Allston Brighton | 1-2 |
| 2/5 | 10:30 am | Charlestown | TriCounty B | 6-0 |
| 2/6 | 5:10 pm | UMass-Boston | Belmont II | 2-1 |
| 2/12 | 5:10 pm | Cleveland Circle | Needham B2 | 3-3 |
| 2/19 | 7:30 pm | Hyde Park | South Boston B | 0-3 |
| February 21-23: District 1 State Tournament Playdowns | ||||
| 2/26 | 8:40 pm | Hyde Park | Hyde Park B1 | 4-1 |
| 3/4 | 4:20 pm | St. Sebastians | Wellesley Covo | 0-2 |