| Squirt I | ||||
| Date | Time | Rink | Opponent | Score |
| October 2-11: 1999 Mayor's Cup Tournament | ||||
| 10/10 | 10:10 am | Hyde Park | Charlestown I | |
| 10/16 | 6:20 pm | Hyde Park | Dorchester I | |
| 10/23 | 8:10 am | Charlestown | Framingham A | 1-3 |
| 10/30 | 9:20 am | Charlestown | Hyde Park I | 6-3 |
| 11/6 | 9:20 am | Charlestown | South Boston A | |
| 11/13 | 9:20 am | Charlestown | Belmont I | |
| 11/14 | 10:20 am | Hyde Park | Needham A | |
| 11/20 | BYE | |||
| 11/27 | 8:10 am | BU | Quincy A | |
| 12/4 | 12:30 pm | NU | TriBoro I | |
| 12/5 | 10:30 am | Quincy | Waltham A | |
| 12/11 | 7:00 am | West Roxbury | Charlestown | 5-2 |
| 12/12 | 10:50 am | Loring | Framingham A | 2-1 |
| 12/18 | 8:10 am | Charlestown | Dorchester I | 7-2 |
| 1/8 | 8:10 am | West Roxbury | Hyde Park I | 5-0 |
| 1/15 | 4:00 pm | Cleveland Circle | South Boston A | 0-2 |
| 1/23 | BYE | |||
| 1/29 | 7:00 am | West Roxbury | Belmont I | |
| 1/30 | 8:40 am | Hyde Park | Needham A | 0-2 |
| 2/5 | 9:20 am | Neponset | TriBoro I | |
| 2/6 | 7:30 am | Hyde Park | Quincy A | 2-0 |
| 2/13 | 9:40 am | Loring | Framingham A | 0-2 |
| 2/19 | 11:00 am | Somerville | Waltham I | |
| February 21-23: District 1 State Tournament Playdowns | ||||
| 2/26 | 5:10 pm | Hyde Park | Wellesley Geary | |
| 3/4 | 7:00 am | West Roxbury | Charlestown I | |
| 3/5 | 8:40 am | Hyde Park | Dorchester I | |
| GBYHL Squirt I Upper Division Playoffs | ||||
| 3/12 | 10:00 am | NU | Belmont I | |
| 3/12 | 3:10 pm | Quincy | Finals | |