| Date | Teams | Event | Venue | Notes |
|---|---|---|---|---|
| 1/4/09 | Bogastow/Prospect vs. SWRT |
GS
|
TBD | Blue Hills or Wachusett Mtn |
| 1/11/09 | Nashoba/Prospect vs. SWRT | GS | Nashoba | |
| 1/18/09 | SWRT vs. Nashoba | SL | Ski Ward | |
| 1/25/09 | SWRT vs. Bogastow | SL | Ski Ward | |
| 2/1/09 | SWRT vs. Bradford | SL | Ski Ward | |
| 2/8/09 | Francis Piche Qualifier | SL & GS | Ski Bradford | |
| 2/8/09 | Kathy Bartolini Fun Race | SL & GS | Nashoba | |
| 2/15/09 | Make-up Date (if needed) | |||
| 2/22/09 | Bradford/Prospect vs. SWRT | SL | Ski Bradford | |
| 3/1/09 | EMBWL Championship | SL & GS | Ski Bradford |