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. Pearl was also a four year letter winner of the Division I baseball team and captained the team his senior year. 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. In 1994 he was named as head coach for his
alma mater. He became just the fifth head hockey coach for the Crusaders and would go on to lead his teams to 9 of the 11 most successful seasons in their history. Holy Cross became a founding member of the
MAAC ice hockey conference in
1998 and Pearl helped the team celebrate by winning a then-team record 22 wins capped off by capturing the inaugural
conference tournament. Unfortunately the MAAC did not possess an automatic bid for the
NCAA tournament and Holy Cross was not invited despite its achievement. As they had done before Holy Cross won the premier conference tournament for the successor
Atlantic Hockey conference but this time were invited to the
2004 tournament. 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. In addition to hockey, Pearl was also the head coach of the
Holy Cross Crusaders baseball team from 1999 to 2001. He coached the first two teams to ever make the post season tournament and was twice named Patriot League coach of the year. In 2014 Pearl resigned as head coach and took a position as the associate head coach with
Harvard. In 2021, Pearl was named the Head Coach at
Cushing Academy, a preparatory school in
Ashburnham, Massachusetts. ==Head coaching record==