Jamaica Plain Regan Youth League: Prior years' champs
Wednesday, August 5Previous Playoff Champs and Division Leaders
2008
| Division | Playoff champs | Division leaders |
| Farm | Power Company | Purple Cactus |
| AA Softball | Boston Building Materials Coop | |
| Juniors | Degrandis Club | Trinidad & Tobago |
| Seniors | City Feed & Supply | Classic Cleaners |
| AAA Softball | Southern JP Health Center | Southern JP Health Center |
| Pony | Coldwell Banker Real Estate Angels |