| Mite I | ||||
| Date | Time | Rink | Opponent | Score |
| October 2-11: 1999 Mayor's Cup Tournament | ||||
| 10/9 | 8:10 am | Hyde Park | Hyde Park I | 9-0 |
| 10/16 | 7:00 am | Charlestown | Belmont I | 2-2 |
| 10/23 | 10:30 am | Hyde Park | Needham A | 1-1 |
| 10/30 | 8:10 am | Hyde Park | South Boston A | 2-3 |
| 10/31 | 8:00 am | Waltham | Wellesley A | 2-3 |
| 11/6 | 7:00 am | Hyde Park | Charlestown I | 4-3 |
| 11/13 | 3:00 pm | Neponset | Dorchester I | 2-2 |
| 11/20 | BYE | |||
| 11/27 | 2:30 pm | Somerville | Quincy A | 3-1 |
| 12/4 | 10:30 am | BU | TriBoro | 3-3 |
| 12/11 | 7:00 am | Waltham | Belmont I | 8-2 |
| 12/12 | 8:30 am | Hyde Park | Hyde Park I | 7-4 |
| 12/18 | 7:00 am | West Roxbury | TriBoro | 4-4 |
| 1/2 | 8:10 am | Quincy | South Boston A | 3-1 |
| 1/9 | 10:50 am | Loring | Framingham A | 5-2 |
| 1/15 | 10:30 am | Charlestown | Charlestown I | 6-1 |
| 1/23 | BYE | |||
| 1/29 | 10:30 am | BU | Wellesley A | 0-2 |
| 2/5 | 7:00 am | West Roxbury | Dedham Open | 7-2 |
| 2/6 | 11:40 am | Neponset | Dorchester I | 4-1 |
| 2/12 | 7:00 am | Neponset | Waltham I | 3-0 |
| 2/19 | 7:00 am | West Roxbury | Somerville A | Cancelled |
| 2/20 | 10:50 am | Loring | Belmont I | 1-1 |
| February 21-23: District 1 State Tournament Playdowns | ||||
| 2/26 | 8:10 am | West Roxbury | Needham A | 1-6 |
| 3/4 | 5:10 pm | Hyde Park | Quincy A | 3-5 |