| PeeWee I | ||||
| Date | Time | Rink | Opponent | Score |
| October 2-11: 1999 Mayor's Cup Tournament | ||||
| 10/9 | 6:20 pm | UMass-Boston | South Boston B (Open) | 2-3 |
| 10/16 | 8:40 pm | Hyde Park | Brookline A | |
| 10/23 | 5:10 pm | Hyde Park | Dedham A | |
| 10/30 | 6:40 pm | St. Sebastians | Framingham B | 2-1 |
| 10/31 | 8:10 am | BU | Dedham A | 1-9 |
| 11/6 | 5:10 pm | Hyde Park | Needham B1 | 6-4 |
| 11/13 | 2:00 pm | St. Sebastians | Somerville A | |
| 11/20 | BYE | |||
| 11/27 | 7:30 pm | Cleveland Circle | TriCounty A | |
| 12/4 | 4:30 pm | St. Sebastians | Brookline A | |
| 12/11 | 8:00 pm | Charlestown | Somerville A | 1-3 |
| 12/12 | 8:30 am | Loring | Framingham B | 6-0 |
| 12/18 | 6:50 pm | St. Sebastians | Brookline A | |
| 1/8 | 8:40 pm | Hyde Park | TriCounty A | 4-2 |
| 1/15 | 2:00 pm | Neponset | Needham B1 | |
| 1/16 | 8:00 am | Cleveland Circle | Brookline A | 4-2 |
| 1/22 | BYE | |||
| 1/29 | 6:50 pm | St. Sebastians | Somerville A | 4-0 |
| 2/6 | 8:30 am | Loring | Framingham B | 4-0 |
| 2/12 | 8:00 pm | St. Sebastians | TriCounty A | 4-6 |
| 2/19 | 8:00 pm | St. Sebastians | Needham B1 | 2-3 |
| February 21-23: District 1 State Tournament Playdowns | ||||
| 2/26 | 3:40 pm | Somerville | Somerville A | 2-2 |
| 2/27 | 8:30 am | Loring | Framingham B | 6-2 |
| 3/4 | 6:40 pm | St. Sebastians | Brookline A | |
| 3/11 | 9:20 am | BU | TriCounty A | |
| GBYHL PeeWee I Lower Division Playoffs | ||||
| 3/19 | 7:00 am | Quincy | Needham B1 | |
| 3/19 | 6:40 pm | Quincy | Finals | |