[1] Pearl began attending Holy Cross in 1985 and played for the Division II program for four years, becoming captain of the team in his senior season.
After graduating Pearl became director of the ice hockey program at Portsmouth Abbey School for two years before returning to college as an assistant at Connecticut under Bruce Marshall.
While Pearl's team was blanked by North Dakota their second berth two years later provided what is widely considered the biggest upset in college hockey history when the 15th seed Crusaders downed the second ranked Minnesota Golden Gophers 4-3 in overtime.
[3] In addition to hockey, Pearl was also the head coach of the Holy Cross Crusaders baseball team from 1999 to 2001.
[4] In 2021, Pearl was named the Head Coach at Cushing Academy, a preparatory school in Ashburnham, Massachusetts.