| Mite II | ||||
| Date | Time | Rink | Opponent | Score |
| October 2-11: 1999 Mayor's Cup Tournament | ||||
| 10/9 | 10:30 am | Hyde Park | Charlestown II | |
| 10/16 | 9:20 am | Hyde Park | Dorchester II | |
| 10/23 | 9:20 am | Hyde Park | Dedham Open | 3-5 |
| 10/30 | 10:30 am | Hyde Park | Hyde Park II | |
| 11/6 | 8:10 am | South Boston | South Boston B | |
| 11/13 | 12:10 am | Quincy-Shea | Brookline A | |
| 11/14 | 8:10 am | Charlestown | Needham B1 | |
| 11/20 | BYE | |||
| 11/27 | 5:20 pm | Neponset | Quincy B | |
| 12/5 | 10:20 am | Waltham | TriCounty Open | |
| 12/11 | 7:00 am | Hyde Park | Belmont II | 9-0 |
| 12/12 | 10:20 am | Cleveland Circle | Waltham II | 4-3 |
| 12/18 | 8:10 am | West Roxbury | Dorchester II | 4-1 |
| 12/19 | 7:20 am | Hyde Park | Needham B2 | 3-6 |
| 1/8 | 8:10 am | Neponset | Hyde Park II | 5-0 |
| 1/15 | 7:00 am | West Roxbury | South Boston B | 3-1 |
| 1/22 | 9:20 am | South Boston | Brookline A | 2-1 |
| 1/23 | 3:25 pm | St. Sebastians | Needham B1 | 2-3 |
| 1/30 | 5:10 pm | Hyde Park | Quincy B | 0-2 |
| 2/12 | 8:10 am | West Roxbury | Needham B2 | |
| 2/19 | 10:30 am | BU | TriCounty Open | Cancelled |
| February 21-23: District 1 State Tournament Playdowns | ||||
| 2/26 | 7:00 am | West Roxbury | Wellesley B | |
| 2/27 | 8:30 am | NU | Dorchester II | 5-2 |
| 3/4 | 4:00 pm | Cleveland Circle | Belmont II | 8-2 |