| Squirt II | ||||
| Date | Time | Rink | Opponent | Score |
| October 2-11: 1999 Mayor's Cup Tournament | ||||
| 10/9 | 8:10 am | Charlestown | South Boston B (Open) | 3-3 |
| 10/16 | 12:50 pm | Neponset | Needham B1 | 1-4 |
| 10/23 | 7:00 am | West Roxbury | Dedham A | |
| 10/30 | 8:10 am | West Roxbury | Brookline A | |
| 11/6 | 4:00 pm | Hyde Park | TriCounty A | |
| 11/7 | 8:10 am | Somerville | Dedham A | |
| 11/13 | 4:00 pm | Hyde Park | Waltham B | |
| 11/20 | BYE | |||
| 11/27 | 8:10 am | Hyde Park | Somerville A | |
| 12/4 | 9:20 am | Hyde Park | Needham B1 | |
| 12/11 | 8:10 am | West Roxbury | Waltham II | 3-2 |
| 12/18 | 5:30 pm | Neponset | Dedham A | |
| 1/2 | 7:30 am | NU | Brookline A | 2-4 |
| 1/8 | 4:30 pm | St. Sebastians | Needham B1 | 1-1 |
| 1/15 | 4:00 pm | Hyde Park | TriCounty A | 0-5 |
| 1/22 | 7:00 am | West Roxbury | Dorchester II | |
| 1/29 | 11:00 am | Somerville | Somerville A | |
| 2/5 | 2:00 pm | Neponset | Wellesley King | 2-5 |
| 2/13 | 7:30 am | Hyde Park | Quincy B | 1-2 |
| 2/19 | 12:10 pm | Somerville | Waltham II | |
| 2/20 | 9:20 am | Somerville | TriCounty A | 0-3 |
| February 21-23: District 1 State Tournament Playdowns | ||||
| 2/26 | 6:20 pm | Cleveland Circle | Brookline A | 3-3 |
| 3/4 | 8:10 am | West Roxbury | Dedham A | |