| Squirt III | ||||
| Date | Time | Rink | Opponent | Score |
| October 2-11: 1999 Mayor's Cup Tournament | ||||
| 10/9 | Cancelled | |||
| 10/16 | 8:10 am | South Boston | Brookline B | 8-0 |
| 10/23 | 10:30 am | Neponset | Dorchester II | 0-10 |
| 10/30 | 10:30 am | Charlestown | Quincy B | 1-7 |
| 11/6 | 3:10 pm | St. Sebastians | Dedham B | 0-2 |
| 11/13 | 7:00 am | Neponset | Belmont II | 0-2 |
| 11/20 | BYE | |||
| 11/27 | 4:10 pm | Neponset | Allston Brighton | 2-2 |
| 12/4 | 1:20 pm | Somerville | TriCounty B | 1-7 |
| 12/5 | 10:50 am | Loring | Wellesley Open | 0-11 |
| 12/11 | 9:20 am | Charlestown | Quincy B | 2-6 |
| 12/18 | 10:30 am | South Boston | Needham B2 | 1-4 |
| 1/8 | 7:00 am | West Roxbury | South Boston B | 0-3 |
| 1/9 | 12:50 pm | Neponset | Belmont II | 3-0 |
| 1/15 | 8:10 am | West Roxbury | TriCounty B | 2-6 |
| 1/16 | 2:30 pm | NU | Needham B2 | 2-4 |
| 1/22 | 8:10 am | West Roxbury | Dedham B | 3-2 |
| 1/23 | 9:10 am | Cleveland Circle | Allston Brighton | 2-2 |
| 2/6 | 4:00 pm | Hyde Park | Hyde Park II | 5-1 |
| 2/12 | 7:00 am | West Roxbury | Wellesley Dowd | |
| 2/20 | 12:50 pm | Quincy | Quincy C | 1-4 |
| February 21-23: District 1 State Tournament Playdowns | ||||
| 2/26 | 4:20 pm | Neponset | Needham B3 | 2-5 |
| 3/5 | 7:00 am | Neponset | Belmont II | |