This is a list of Grey Cup winning head coaches. Head Coaches with multiple Grey Cup wins {| class="wikitable sortable" style="font-size: 95%; text-align:center" |- ! Head Coach ! Wins ! Years won ! Team(s) |- |Lew Hayman |5 |1933, 1937, 1938, 1942, 1949 |Toronto Argonauts, Toronto RCAF Hurricanes, Montreal Alouettes |- |Frank Clair |5 |1950, 1952, 1960, 1968, 1969 |Toronto Argonauts, Ottawa Roughriders |- |Hugh Campbell |5 |1978, 1979, 1980, 1981, 1982 |Edmonton Eskimos |- |Don Matthews |5 |1985, 1995, 1996, 1997, 2002 |BC Lions, Baltimore Stallions, Toronto Argonauts, Montreal Alouettes |- |Wally Buono |5 |1992, 1998, 2001, 2006, 2011 |Calgary Stampeders, BC Lions |- |Billy Hughes |4 |1922, 1923, 1924, 1932 |Queen's University, Hamilton Tigers |- |Bud Grant |4 |1958, 1959, 1961, 1962 |Winnipeg Blue Bombers |- |Liz Marriott |3 |1912, 1913, 1915 |Hamilton Alerts, Hamilton Tigers |- |Teddy Morris |3 |1945, 1946, 1947 |Toronto Argonauts |- |Pop Ivy |3 |1954, 1955, 1956 |Edmonton Eskimos |- |Ralph Sazio |3 |1963, 1965, 1967 |Hamilton Tiger-Cats |- |Marc Trestman |3 |2009, 2010, 2017 |Montreal Alouettes,Toronto Argonauts |- |Harry Griffith |2 |1909, 1910 |University of Toronto |- |Dave McCann |2 |1925, 1926 |Ottawa Senators |- |Mike Rodden |2 |1928, 1929 |Hamilton Tigers |- |Art Massucci |2 |1934, 1936 |Sarnia Imperials |- |Red Threlfall |2 |1939, 1941 |Winnipeg Blue Bombers |- |Marv Levy |2 |1974, 1977 |Montreal Alouettes |- |Mike Riley |2 |1988, 1990 |Winnipeg Blue Bombers |- |Ron Lancaster |2 |1993, 1999 |Edmonton Eskimos, Hamilton Tiger-Cats |- |John Hufnagel |2 |2008, 2014 |Calgary Stampeders |- |Mike O'Shea |2 |2019, 2021 |Winnipeg Blue Bombers head coach