5 Winningest coaches in Toronto Maple Leafs history, ft. Sheldon Keefe

The Toronto Maple Leafs are one of the oldest teams in the NHL, joining alongside the Montreal Canadiens in 1917. Moreover, the franchise has the second most Stanley Cup championships with 13, trailing the Canadiens, who own the league record with 24 titles.

Throughout its illustrious 106-season history, Toronto has employed 40 different head coaches, with Sheldon Keefe currently serving in the role, taking over from Mike Babcock on Nov. 19, 2019.

Although he's only been on the job for five seasons, Keefe has climbed the team's all-time coaching ranks, winning more games than 35 other coaches who took a turn behind the bench.

Today, we look at the winningest coaches in the Maple Leafs history.

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Winningest coaches in Toronto Maple Leafs history

#5 Sheldon Keefe (2019 - Present)

Coaching record: 187-84-38

As mentioned, Keefe rose through the Maple Leafs system, helping their AHL team, the Toronto Marlies, win the Calder Cup in 2017-18, eventually earning a promotion to the NHL and taking over the Original Six franchise in 2019.

Sheldon Keefe, Toronto Maple Leafs

In just five seasons, thanks to the help of superstar players like Auston Matthews and Mitch Marner, Keefe has already collected the fifth most wins, becoming one of six coaches to surpass 150 victories with the club while maintaining the highest win percentage (.667).

#4 Dick Irvin (1932 - 1940)

Coaching record: 216-152-59

Dick Irvin was the 12th head coach in Maple Leafs history, serving behind the bench from 1932 to 1940, winning the Stanley Cup in his first season. Although he would lead the Canadiens to four championships after leaving Toronto, he remains one of the Leafs' top coaches in games (fourth), regular season wins (fourth) and playoff wins (fourth).

Before becoming a coach, Irvin played 95 matchups with the Chicago Blackhawks from 1926 to 1929, finishing fourth in Hart Trophy voting his rookie season.

#3 Hap Day (1941 - 1950)

Coaching record: 259-206-81

Although Hap Day is not the winningest coach in franchise history, it could be argued that he is the most successful, leading Toronto to Stanley Cup titles in 1942, 1945, 1947, 1948 and 1949 while winning an additional one as assistant general manager in 1951.

After serving as Toronto's captain from 1925 until 1937, Day retired from the NHL in 1938 after a season with the New York Americans, rejoining the Maple Leafs as head coach three seasons later. He remains the second longest-tenured bench boss in franchise history, serving for ten seasons.

#2 Pat Quinn (1999 - 2006)

Coaching record: 300-196-52-26

Pat Quinn played 606 games as a defenseman in the NHL before becoming an assistant coach immediately following his retirement in 1977. Eventually, he earned head coaching jobs and served as president and general manager with the Vancouver Canucks before coming to the Maple Leafs in 1999.

Pat Quinn, Toronto Maple Leafs

By the time he made it to Toronto, Quinn was already a two-time Jack Adams Award winner and, in just seven seasons, had become the fastest head coach in team history to collect 300 wins, achieving the milestone in just 574 games. Despite great regular seasons, his teams only advanced past the second round once, missing the playoffs in 2006, resulting in his dismissal.

#1 Punch Imlach (1959 - 1969, 1979 - 1980)

Coaching record: 370-275-125

Punch Imlach became the general manager of the Maple Leafs in 1958 and promoted himself to the head coaching job in November of that year. During his first tenure, which lasted ten seasons, he guided the team to four Stanley Cup titles in 1962, 1963 and 1964, and their most recent championship in 1967.

After the 1969 season, he left to pursue a role with the Buffalo Sabres, only to return a decade later in 1979 to serve as general manager, assuming a head coaching role (again) for ten games.

Imlach is the winningest coach in team history and the only one to surpass 350 regular season wins while coming the closest to 50 playoff wins, finishing with a 49-31 record in the postseason.