 Cooley earned his first head coaching position in 2006 for Fairfield University of the Metro Atlantic Athletic Conference.In five seasons, Cooley's teams posted a 92–69 overall record and 58–32 conference record.In 2009–10, with a 23–11 record, Fairfield advanced to postseason play, setting an NCAA Division I postseason record by overcoming a 27-point halftime deficit to win in overtime over George Mason in the 2010 CollegeInsider.com Tournament.