With Cavallaro as the offensive coordinator, the Quakers advanced to the NCAA playoffs in 2004 after a 17-year absence from NCAA postseason competition. The 2006 edition of Penn lacrosse also worked its way into the Division I Championship Tournament.
A 1994 graduate of Johns Hopkins University, Cavallaro was a four-year starter and two-year captain for the Blue Jays. He immediately jumped into the coaching ranks, spending four seasons on the sidelines as the head assistant coach and offensive coordinator at Washington College (Md.), where he helped the Shoremen to the 1996, 1997, and 1998 NCAA Division III Championship games.
Following the 1998 season at Washington, Cavallaro was named the offensive coordinator at his alma mater. While coaching at Hopkins, the Jays advanced to the Final Four in 1999 and 2000. After Johns Hopkins, Cavallaro spent three seasons as the head assistant coach and offensive coordinator at the University of North Carolina.