The Stanley Cup, or The Holy Grail, is the oldest existing trophy to be awarded to a professional sports franchise in the entirety of North America and is also considered as the most important championship available to the sport by the International Ice Hockey Federation. Moreover, it was donated Lord Stanley of Preston, the Governor General of Canada who was highly enthusiastic about ice hockey and was highly impressed later on by the game played at the 1889 Winter Carnival. Soon, it was awarded to the top ranking amateur ice hockey club in Canada before making its way to the National Hockey League (NHL). Notably, it has been awarded 106 times till now with 25 teams winning the coveted trophy.
NHL Coaches with Stanley Cup-
Till date, there have been 56 coaches who have claimed the Stanley Cup Championship, out of many of them have claimed it more than once. Remarkably, Scotty Bowman leads the chart with the coach with the most Stanley Cup wins (9) and appearances (13) till date. However, his overall Stanley Cup count is 14, which includes his wins as a head coach, assistant coach, and as an executive. Bowman also holds the record for most wins in league history, with 1,244 wins in regular season and 223 playoff wins. Toe Blake is the second head coach in the list, with eight Stanley Cup championships in 10 appearances followed by Hap Day with five Stanley Cups in eight appearances
The following table gives a glimple into all 56 coaches who have won the Stanley Cup till date:
| Head Coach | Stanley Cups | Final Appearances | Years Won |
| Scotty Bowman | 9 | 13 | 1973, 1976, 1977, 1978, 1979, 1992, 1997, 1998, 2002 |
| Toe Blake | 8 | 10 | 1956, 1957, 1958, 1959, 1960, 1965, 1966, 1968 |
| Hap Day | 5 | 8 | 1942, 1945, 1947, 1948, 1949 |
| Al Arbour | 4 | 7 | 1980, 1981, 1982, 1983 |
| Glen Sather | 4 | 6 | 1984, 1985, 1987, 1988 |
| Punch Imlach | 4 | 7 | 1962, 1963, 1964, 1967 |
| Dick Irvin | 4 | 5 | 1932, 1944, 1946, 1953 |
| Tommy Ivan | 3 | 5 | 1950, 1952, 1954 |
| Lester Patrick | 3 | 3 | 1925, 1928, 1933 |
| Jack Adams | 3 | 5 | 1925, 1928, 1933 |
| Joel Quenneville | 3 | 4 | 2010, 2013, 2015 |
| Pete Green | 3 | 5 | 1920, 1921, 1923 |
| Tommy Gorman | 2 | 3 | 1934, 1935 |
| Art Ross | 2 | 3 | 1929, 1939 |
| Mike Sullivan | 2 | 2 | 2016, 2017 |
| Fred Shero | 2 | 2 | 1974, 1975 |
| Cecil Hart | 2 | 2 | 1930, 1931 |
| Darryl Sutter | 2 | 2 | 2012, 2014 |
| Jon Cooper | 2 | 2 | 2020, 2021 |
| Pat Burns | 1 | 1 | 2003 |
| Ken Hitchcock | 1 | 1 | 1999 |
| Jacques Lemaire | 1 | 1 | 1995 |
| Joe Primeau | 1 | 1 | 1951 |
| Jean Perron | 1 | 1 | 1986 |
| Barry Trotz | 1 | 1 | 2018 |
| Jacques Demers | 1 | 1 | 1993 |
| Larry Robinson | 1 | 1 | 2000 |
| Jared Bednar | 1 | 1 | 2022 |
| Al MacNeil | 1 | 1 | 1971 |
| Dan Bylsma | 1 | 1 | 2009 |
| Peter Laviolette | 1 | 1 | 2006 |
| Dave Gill | 1 | 1 | 1927 |
| Eddie Gerard | 1 | 1 | 1926 |
| Terry Crisp | 1 | 1 | 1989 |
| Dick Carroll | 1 | 1 | 1918 |
| Randy Carlyle | 1 | 1 | 2007 |
| Marc Crawford | 1 | 1 | 1996 |
| John Tortorella | 1 | 1 | 2004 |
| Bob Hartley | 1 | 1 | 2001 |
| Bob Johnson | 1 | 1 | 1991 |
| Cooney Weiland | 1 | 1 | 1941 |
| Mike Babcock | 1 | 1 | 2008 |
| Tom Johnson | 1 | 1 | 1972 |
| Leo Dandurand | 1 | 1 | 1924 |
| Mike Keenan | 1 | 1 | 1994 |
| George O'Donoghue | 1 | 1 | 1922 |
| Harry Sinden | 1 | 1 | 1970 |
| Claude Julien | 1 | 1 | 2011 |
| Rudy Pilous | 1 | 1 | 1961 |
| Bill Stewart | 1 | 1 | 1938 |
| Jimmy Skinner | 1 | 1 | 1955 |
| Claude Ruel | 1 | 1 | 1969 |
| John Muckler | 1 | 1 | 1990 |
| Frank Boucher | 1 | 1 | 1940 |
| Craig Berube | 1 | 1 | 2019 |
| Bruce Cassidy | 1 | 1 | 2023 |
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