Caufield scored his 50th goal of the 2025-26 season in a 2-1 win for the Montreal Canadiens against the Tampa Bay Lightning at Bell Centre on April 9, 2026. He reached the milestone at 6:30 of the second period to become the seventh player in Canadiens history to score 50 goals in a season and first since Stephane Richer scored 51 in 1989-90. He was also the first United States-born player to score 50 goals in a season for Montreal and scored his 29th go-ahead goal of the season, the second-most in NHL history behind Brett Hull's 39 for the St. Louis Blues in 1990-91.

Caufield was named a finalist for the 2026 Lady Byng Trophy given annually to the player voted best to combine sportsmanship, gentlemanly conduct and ability as voted on by the Professional Hockey Writers Association.

The No. 15 pick by the Canadiens in the 2019 NHL Draft, Caufield's older brother, Brock Caufield, played at the University of Wisconsin. Their father, Paul Caufield, played NCAA Division III hockey at the University of Wisconsin-Stevens Point. Their grandfather, Wayne Caufield, was a 2011 inductee into the Wisconsin Hockey Hall of Fame who spent more than two decades coaching youth hockey and managing hockey clinics in the Milwaukee area.

Cole Caufield won the 2021 Hobey Baker Award, voted as the top men's player in NCAA Division I ice hockey. As a sophomore at Wisconsin, he led NCAA Division I in goals (30), points (52), power-play goals (11), power-play points (24) and shots on goal (165) and was named Big Ten Player of the Year. He also scored five points (two goals, three assists) in seven games to help the United States win the 2021 IIHF World Junior Championship.

After scoring 88 points (49 goals, 39 assists) in 67 games in two NCAA seasons, Caufield signed a three-year, entry-level contract with the Canadiens on March 27, 2021, and made his NHL debut in a 2-1 win against the Calgary Flames on April 26.

Caufield scored his first NHL goal May 1 against the Ottawa Senators, and his first goal in the Stanley Cup Playoffs on June 14, a 4-1 loss to the Vegas Golden Knights in Game 1 of the Stanley Cup Semifinals.

Caufield signed an eight-year, $62.8 million contract to stay with the Canadiens on June 5, 2023, in lieu of becoming an restricted free agent.