| PeeWee III | ||||
| Date | Time | Rink | Opponent | Score |
| October 2-11: 1999 Mayor's Cup Tournament | ||||
| 10/9 | 5:30 pm | Neponset | South Boston D | 2-4 |
| 10/17 | 8:10 am | Charlestown | Hyde Park II | 0-6 |
| 10/23 | 7:30 pm | Cleveland Circle | Belmont III | 4-2 |
| 10/31 | 8:00 am | NU | Wellesley Tracy | 1-0 |
| 11/6 | 8:40 pm | Cleveland Circle | Dedham B | 7-1 |
| 11/13 | 6:20 pm | Cleveland Circle | Framingham C2 | 1-0 (Forfeit) |
| 11/14 | 4:20 pm | Neponset | South Boston C | 3-5 |
| 11/20 | BYE | |||
| 11/28 | 10:30 am | Neponset | Needham B3 | |
| 12/4 | 5:10 pm | Hyde Park | Quincy C | |
| 12/11 | BYE | |||
| 12/19 | 4:00 pm | Neponset | Hyde Park B2 | 0-4 |
| 1/2 | 4:00 pm | Neponset | Belmont III | 2-8 |
| 1/9 | 5:10 pm | UMass-Boston | Wellesley Tracy | 5-5 |
| 1/16 | 5:10 pm | UMass-Boston | Dedham B | 4-3 |
| 1/22 | 10:30 am | Charlestown | Framingham C2 | 4-0 |
| 1/23 | 5:10 pm | UMass-Boston | South Boston C | 0-5 |
| 1/30 | 6:20 pm | UMass-Boston | Needham B3 | |
| 2/12 | 7:30 pm | Hyde Park | Quincy C | 1-5 |
| 2/20 | 4:00 pm | Neponset | Waltham III | 1-8 |
| February 21-23: District 1 State Tournament Playdowns | ||||
| 2/27 | 5:10 pm | Hyde Park | Brookline C | |
| 3/5 | 7:00 am | Somerville | South Boston D | |