Caufield played youth hockey in Milwaukee for the SHAW program. As a senior, he led the WAHA team to its only Senior Class Tournament championship. Following a season with the Madison Capitols junior program, Caufield enrolled at the University of Wisconsin-Stevens Point.
In four years at UW-Stevens Point, Caufield became the school’s all-time leading scorer with 254 points and 126 goals in 148 games. He was named an All-American in his junior and senior years. He helped lead his team to three straight national championships from 1989–1991.
After several years coaching at the high school and collegiate ranks, Caufield is now the rink manager in Stevens Point. He is a WAHA regional director and involved in the WAHA coaching program.
In 2012, Caufield was one of 18 players selected to the all-time WIAC hockey team. He is the only Wisconsin born player on the list.