Although he attended the University of North Dakota, Caufield played football, not hockey, with the program there. It was only after graduating that he signed with the Rangers and was assigned to Toledo of the IHL.
The following year, 1986-87, he saw his first NHL action and established himself with 45 penalty minutes in 13 games. His was not going to be a game of finesse and skill, but rather one of toughness.
Nevertheless, the Rangers traded Caufield prior to the 1987-88 season, but he played only one game for Minnesota before landing in Pittsburgh the next year where he had his greatest success.
With the Pens, Caufield played most of five seasons, including the 1991-92 Cup-winning year. Along the way, he averaged nearly four penalty minutes a game, and in 194 games with Pittsburgh he scored a grand total of three goals. He was demoted to the "I" for 1993-94 and retired at year's end.