Born in Hamilton, Ontario, Irvin was one of the greatest players of his day, balancing a torrid slapshot and tough style with gentlemanly play. He played junior and senior amateur hockey in Winnipeg, Manitoba, winning the Allan Cup in 1915 with the Winnipeg Monarchs. He began his professional career in 1916 with the Portland Rosebuds of the Pacific Coast Hockey Association and was the fourth leading scoring rookie tallying 35 goals. Following a brief stint in the Canadian Army, he was reinstated as an amateur, but turned professional again in 1921 with the Regina Capitals of the Western Canada Hockey League. In 1926, at age 34, he entered the NHL, signed by the newly formed Chicago Black Hawks. Irvin was made the team's first captain, and had an impressive campaign, finishing second in the league in scoring. In their first season, the Black Hawks led all NHL teams in scoring, led by Irvin and Babe Dye. Irvin's second season turned to tragedy as he fractured his skull, which led to retirement after the 1928-29 season. The Hawks had finished with the worst record in the NHL in both of his last two seasons as a player.
Irvin was hired as head coach of the Black Hawks in 1930, and in his first season behind the bench led the team to 24 wins, 17 losses and 3 ties. Upon seeing his success as a coach, Toronto Maple Leafs owner Conn Smythe convinced Irvin to coach the Leafs. In his first season coaching the Leafs (the first in the brand-new Maple Leaf Gardens), he achieved immediate success by winning the Stanley Cup. However, Irvin was unable to deliver another Cup for the Leafs during his time as coach, despite taking them to the finals six more times.
Smythe soon felt that Irvin had taken the Leafs as far as he could, and suggested to the Canadian Arena Company, owners of the then-moribund Montreal Canadiens, that they hire Irvin as coach in 1940. It was there that Irvin found his greatest success, leading the Habs to three Cups in six finals. Helped by star players Elmer Lach, Doug Harvey, goalie Bill Durnan and a young Maurice Richard, the Canadiens were just beginning to blossom as an NHL dynasty.
Irvin, however, came under fire for encouraging "goon" tactics, especially after Montreal fans rioted in protest of Richard's suspension for the 1955 playoffs. He was already well known for looking the other way when stick-swinging duels broke out in practices. Although they made it to the finals (losing to the Detroit Red Wings), internal pressure forced Irvin to step down.
He returned to the Black Hawks as head coach for the 1955-56 season, taking the reins of a moribund team that had only made the playoffs once in the past 10 years and finished last in the past two seasons. Irvin was unable to turn the team's fortunes around, and the Black Hawks again ended the year in last place, despite the emergence of Ed Litzenberger as a scoring star. Irvin was to coach the Black Hawks again in 1956-57, but he became so ill with bone cancer that he had to retire before the season began. He died a few months later at age 64.
A year later, Irvin was elected into the Hockey Hall of Fame. His coaching career included four Stanley Cups with 692 regular season wins, results surpassed only by Al Arbour and Scotty Bowman.
His son, Dick Irvin, Jr., is a noted Canadian television sports announcer.