[2] He won his 800th game in 2009 and finished his NCAA Division I career with 873 victories, ranking 11th all time as of February 2019.

After his father died of a heart attack when Calhoun was 15, he was left to watch over his large family that included five siblings.

Although he received a basketball scholarship to Lowell State, he only attended the school for three months after which he returned home to help support his mother and siblings.

In 1970, Calhoun accepted a position at Dedham High School as a history / social studies teacher and began building a very strong program.

[7] In the two years before Calhoun began coaching, the basketball team had only won five games in the previous two seasons.

[7] During the Bay State Conference championship game, there were two seconds left on the clock when the Marauders were playing Needham High School.

[8][9] The team entered the TECH Tournament as the number one seed but lost to North Quincy High School in the semifinals at the Boston Garden.

Former Boston Celtics captain Reggie Lewis, who played for Calhoun at Northeastern, was a first-round pick in the 1987 NBA draft.

After completing his first season just 9–19, Calhoun led the Huskies to a 20–14 record in 1988 and a bid to National Invitation Tournament, where they defeated Ohio State to win the NIT championship.

Earlier that year, Calhoun had passed Hugh Greer to become the winningest coach in UConn history.

During the Jim Calhoun era, the Huskies did well in the Big East Conference with an impressive 220–112 record (.665 winning percentage).

His friend and Big East rival coach Jim Boeheim also won his 700th game during the previous week.

Later in 2005, Coach Calhoun was honored by induction into the Naismith Memorial Basketball Hall of Fame, fittingly, along with Boeheim.

The victory over Butler made Calhoun, at 68, the oldest coach to win an NCAA Division I men's basketball title.

In March 2009, the NCAA investigated potential violations in UConn's recruitment of Nate Miles (a scholarship recipient expelled without playing a single game for the Huskies).

As a result, in February 2011, Calhoun was cited by the NCAA for failing to create an atmosphere of compliance and suspended for the first three Big East games of 2011–2012 season.

On February 22 Jim Calhoun returned to the sidelines for the team's matchup with St. John's at Gampel Pavilion, only 16 days after the surgery.

[19] He returned on March 3, 2012, less than a week after having back surgery, to coach the team to a win over Pittsburgh in the final game of the regular season.

[23] On September 18, 2018, Calhoun was named the first head coach of the men's basketball team at the University of Saint Joseph (USJ), an NCAA Division III program in West Hartford, Connecticut.

[24] Calhoun's 2019–20 team at USJ had a 25-game winning streak before losing in the first round of the Division III postseason tournament.