[16] During the aforementioned season, Caufield led the entire NCAA with 30 goals and 52 points in 31 games and became the first back-to-back Big Ten scoring champion.

[21] Appearing in two AHL games for Laval, Caufield was recalled to the Canadiens' taxi squad on April 16 but was unable to be assigned to the active roster due to salary cap issues.

[22] Following injuries to teammates Paul Byron and Jonathan Drouin, Caufield made his NHL debut as an emergency recall in a 2–1 victory over the Calgary Flames on April 26.

[32] Entering the 2021–22 NHL season as a favorite to win the Calder Memorial Trophy,[33][34] Caufield struggled amidst the Canadiens' poor start, recording just a single assist in his first ten games.

After the midseason replacement of head coach Dominique Ducharme with retired NHL star forward Martin St. Louis in February 2022, Caufield quickly saw his ice time increase under the foregoing, returning to the team's top line alongside Nick Suzuki and Josh Anderson.

[42] On March 15, Caufield scored two goals in eight seconds in a game against the Arizona Coyotes, the fastest two-goal performance for the Canadiens franchise since Stéphane Richer in 1987.

With Caufield and Suzuki an established duo on the team's first line, head coach St. Louis began experimenting with different players in the other winger slot.

The early games saw Anderson, Sean Monahan and Mike Hoffman rotate through the position, before being given to the recently acquired Kirby Dach, the former 2019 third overall selection whom held initial expectation as a centerman.

[51] His 40 goals through his first 100 games was the fourth-highest for a Canadiens player in the preceding nine decades, behind only honored team members and Hockey Hall of Fame inductees Maurice "Rocket" Richard, Jean Béliveau, and Bernie Geoffrion.

[52] After scoring 26 goals and 10 assists in 46 games, it was announced on January 21 that Caufield required surgery for a shoulder injury that he had been playing through for some time, resulting in a premature end to his season.

[54] With hopes of continuing his scoring pace from the first half of the prior campaign, he would unexpectedly record the lowest shooting percentage of his career.

[63] In 2017, Caufield was selected to the World U-17 Hockey Challenge (U17 WHC), where he tallied eight goals and five assists in six games, leading the United States to a gold medal.

[67] On April 27, 2019, Caufield tied Alex Ovechkin's single tournament goals record with 14 at the 2019 IIHF World U18 Championship (U18 WJC), en route to a bronze medal.

[70] Following the 2023–24 NHL season, with the Canadiens failing to qualify for the 2024 Stanley Cup playoffs, Caufield accepted an invitation to make his senior national team debut at the 2024 IIHF World Championship.

[73] Caufield has an older brother, Brock, who likewise played for the Wisconsin Badgers men's ice hockey team,[74] and is currently a member of the Reading Royals in the ECHL.

[76][77] He returned to UWSP in 2002 to work as an assistant coach, but resigned in 2006 to assume his current position as manager of Ice Hawks Arena.