| Squirt IV | ||||
| Date | Time | Rink | Opponent | Score |
| October 2-11: 1999 Mayor's Cup Tournament | ||||
| 10/10 | 11:30 am | Waltham | Hyde Park II | 1-10 |
| 10/17 | 10:20 am | Hyde Park | Hyde Park III | 1-3 |
| 10/24 | 9:20 am | Charlestown | Quincy C | 0-9 |
| 10/30 | 9:20 am | South Boston | Dorchester III | 0-4 |
| 11/6 | 10:30 am | South Boston | Needham B3 | 0-10 |
| 11/13 | 10:30 am | South Boston | South Boston C | 0-5 |
| 11/14 | 1:45 pm | NU | Wellesley B | 0-11 |
| 11/21 | BYE | |||
| 11/28 | 7:00 am | Somerville | Hyde Park II | 1-3 |
| 12/4 | 10:30 am | South Boston | Belmont III | 3-3 |
| 12/5 | 2:15 pm | St. Sebastians | Brookline C | 7-1 |
| 12/11 | 8:10 am | South Boston | Brookline B | 3-0 |
| 12/12 | 5:10 pm | Neponset | Brookline C | 5-2 |
| 12/18 | 10:30 am | BU | Brookline C | 2-0 |
| 1/8 | 10:30 am | South Boston | Hyde Park III | 7-3 |
| 1/9 | 3:25 pm | St. Sebastians | Charlestown II | 1-6 |
| 1/15 | BYE | |||
| 1/22 | 2:30 pm | Somerville | Waltham IV | 4-4 |
| 1/23 | 9:40 am | Loring | Framingham White | 0-3 |
| 1/29 | 8:10 am | West Roxbury | South Boston C | 5-6 |
| 2/5 | 8:10 am | West Roxbury | Dorchester III | 0-7 |
| 2/12 | 1:20 pm | Somerville | Belmont III | 1-1 |
| 2/19 | 8:10 am | West Roxbury | Waltham IV | Cancelled |
| February 21-23: District 1 State Tournament Playdowns | ||||
| 2/26 | 9:20 am | Neponset | Brookline B | 4-2 |
| 3/4 | 11:00 am | Somerville | Hyde Park III | 5-4 |
| 3/5 | 10:30 am | Somerville | Charlestown II | 7-6 |
| GBYHL Squirt II Division Playoffs | ||||
| 3/11 | 6:40 pm | St. Sebastians | Dorchester III | |
| 3/12 | 12:50 pm | Quincy | Finals | |