The Double A (AA) Division is the first year in which players pitch in real games. Games are played on a 60' diamond and 46' foot mound. Players receive full uniforms and the teams are named after real Minor League teams.

Games are Mondays and Thursdays at 5:30 - 7:00 PM and some weekends at various times. Fields are located throughout Winchester, mainly at Nutile Field and McDonald Field.

This level is for 8 and 9-year-old players as of April 30th.