Loyalties to a team can run deep – whether from childhood, or from the moment they are drafted to a new team. But in the case of a century-old rivalry, where loyalty already runs deep, this loyalty is challenged when a trade or free agency dictates that you play on both sides of that rivalry.
Only 108 players and two coaches have ever put on both the bleu, blanc et rouge of Les Canadiens as well as the blue and white of Toronto, with notable names such as Hall of Famers Jacques Plante, Dick Duff, Frank Mahovlich, George Hainsworth and Doug Gilmour.
Total seasons spent with team listed, with years in parentheses.
| Montréal | ACTIVE PLAYERS (3) | Toronto |
|---|---|---|
| 3 (2016-19) | Jordie Benn | 1 (2022-) |
| 1 (2020-21) | Erik Gustafsson | 1 (2022-) |
| 4 (2017-21) | Victor Mete | 1 (2022-) |
| Montréal | SKATERS (96) | Toronto |
|---|---|---|
| 1 (2018-19) | Kenny Agostino | 1 (2020-21) |
| 3 (1918-21) | Amos Arbour | 1 (1923-24) |
| 1 (2012-13) | Colby Armstrong | 2 (2010-12) |
| 1 (2002-03) | François Beauchemin | 2 (2009-11) |
| 1 (2001-02) | Sergei Berezin | 5 (1996-2001) |
| 4 (1984-88) | Serge Boisvert | 1 (1982-83) |
| 3 (1932-35) | Léo Bourgault | 1 (1926-27) |
| 1 (2021-22) | Adam Brooks | 2 (2019-21) |
| 1 (2015-16) | Mike Brown | 3 (2010-13) |
| 1 (1981-82) | Jeff Brubaker | 2 (1984-86) |
| 1 (1919-20) | Harry Cameron | 2 (1917-19) 1 (1919-20) 4 (1919-23) |
| 2 (1940-42) 6 (1943-49) |
Murph Chamberlain | 3 (1937-40) |
| 4 (1921-25) | Sprague Cleghorn | 1 (1920-21) |
| 5 (1917-22) | Bert Corbeau | 4 (1923-27) |
| 7 (1985-92) 4 (1996-2000) |
Shayne Corson | 3 (2000-03) |
| 1 (1919-20) | Jack Coughlin | 1 (1917-18) |
| 4 (1988-92) | Russ Courtnall | 6 (1983-89) |
| 1 (2002-03) | Mariusz Czerkawski | 1 (2005-06) |
| 7 (1992-99) | Vincent Damphousse | 5 (1986-91) |
| 1 (1982-83) | Dan Daoust | 8 (1982-90) |
| 1 (1950-51) | Bob Dawes | 3 (1946-50) |
| 2 (1984-86) | Lucien DeBlois | 2 (1990-92) |
| 1 (1990-91) | Gerald Diduck | 1 (1999-2000) |
| 4 (1991-95) | Paul DiPietro | 2 (1994-96) |
| 1 (1942-43) | Gordie Drillon | 6 (1936-42) |
| 6 (1964-70) | Dick Duff | 10 (1954-64) |
| 1 (1951-52) | Garry Edmundson | 2 (1959-61) |
| 1 (2017-18) | Byron Froese | 2 (2015-17) |
| 6 (2012-18) | Alex Galchenyuk | 1 (2020-21) |
| 4 (1950-54) 1 (1955-56) |
Dick Gamble | 2 (1965-67) |
| 3 (2009-12) | Hal Gill | 2 (2006-08) |
| 2 (2001-03) | Doug Gilmour | 6 (1991-97) 1 (2002-03) |
| 4 (1979-83) 3 (1985-88) |
Gaston Gingras | 3 (1982-85) |
| 2 (2006-08) | Mikhail Grabovski | 5 (2008-13) |
| 1 (1938-39) | Bob Gracie | 3 (1930-33) |
| 2 (2002-04) | Ron Hainsey | 2 (2017-19) |
| 1 (1941-42) | Red Heron | 3 (1938-41) |
| 1 (1968-69) | Larry Hillman | 8 (1960-68) |
| 2 (1997-99) | Jonas Hoglund | 4 (1999-2003) |
| 1 (1956-57) | Bronco Horvath | 1 (1962-63) |
| 1 (1934-35) 1 (1936-37) |
Roger Jenkins | 1 (1930-31) |
| 1 (2006-07) | Mike Johnson | 4 (1996-2000) |
| 2 (2011-13) | Tomas Kaberle | 12 (1998-2011) |
| 4 (2000-04) | Chad Kilger | 4 (2003-08) |
| 3 (1981-84) | Bill Kitchen | 1 (1984-85) |
| 6 (2002-09) | Mike Komisarek | 4 (2009-13) |
| 4 (1985-89) | John Kordic | 3 (1988-91) |
| 3 (1984-87) | Tom Kurvers | 2 (1989-91) |
| 1 (1983-84) | Larry Landon | 1 (1984-85) |
| 1 (1981-82) | Craig Laughlin | 1 (1988-89) |
| 2 (1992-94) | Gary Leeman | 9 (1983-92) |
| 3 (1989-92) | Sylvain Lefebvre | 2 (1992-94) |
| 3 (1952-55) | Ed Litzenberger | 3 (1961-64) |
| 2 (1988-90) | Jyrki Lumme | 2 (2001-03) |
| 1 (1945-46) | Vic Lynn | 4 (1946-50) |
| 1 (1961-62) | Al MacNeil | 4 (1955-60) |
| 4 (1970-74) | Frank Mahovlich | 12 (1956-68) |
| 3 (1996-99) | Dave Manson | 2 (2000-02) |
| 10 (1951-63) | Don Marshall | 1 (1971-72) |
| 5 (1950-55) |
Paul Masnick | 1 (1957-58) |
| 1 (1925-26) | Joe Matte | 1 (1919-20) |
| 2 (1929-31) | Bert McCaffrey | 4 (1924-28) |
| 3 (1951-54) | John McCormack | 4 (1947-51) |
| 2 (1917-19) 1 (1920-21) 1 (1921-22) |
Jack McDonald | 1 (1920-21) |
| 1 (1969-70) | Larry Mickey | 1 (1968-69) |
| 4 (1983-88) | Sergio Momesso | 1 (1995-96) |
| 2 (1967-69) | Garry Monahan | 5 (1970-75) 1 (1978-79) |
| 12 (1951-63) | Dickie Moore | 1 (1964-65) |
| 1 (2009-10) | Dominic Moore | 2 (2007-09) 1 (2017-18) |
| 4 (1991-95) | Kirk Muller | 2 (1995-97) |
| 1 (1920-21) | Harry Mummery | 2 (1917-19) |
| 3 (1982-85) | Ric Nattress | 1 (1991-92) |
| 4 (2007-11) | Ryan O’Byrne | 1 (2012-13) |
| 8 (1950-58) | Bert Olmstead | 4 (1958-62) |
| 1 (2014-15) | P.A. Parenteau | 1 (2015-16) |
| 2 (1927-29) | George Patterson | 2 (1926-28) |
| 3 (2001-04) | Yanic Perreault | 1 (1993-94) 3 (1998-2001) 1 (2006-07) |
| 4 (1980-84) | Robert Picard | 1 (1980-81) |
| 14 (2003-18) 1 (2018-19) |
Tomas Plekanec | 1 (2017-18) |
| 2 (1965-67) | Noel Price | 2 (1957-59) |
| 2 (1992-94) | Rob Ramage | 2 (1989-91) |
| 1 (1963-64) | Marc Réaume | 6 (1954-60) |
| 3 (1920-26) | Dave Ritchie | 1 (1918-19) |
| 3 (1999-2002) | Stéphane Robidas | 1 (2014-15) |
| 2 (1982-84) | Bill Root | 3 (1984-87) |
| 4 (1939-43) | Charlie Sands | 2 (1932-34) |
| 7 (1987-95) 1 (2008-09) |
Mathieu Schneider | 3 (1995-98) |
| 1 (1977-78) | Rod Schutt | 1 (1985-86) |
| 1 (2000-01) | Darryl Shannon | 5 (1988-93) |
| 1 (1952-53) | Gaye Stewart | 4 (1942-48) |
| 3 (1986-89) | Gilles Thibaudeau | 2 (1989-91) |
| 1 (1939-40) | Rhys Thomson | 1 (1942-43) |
| 4 (1996-2000) | Scott Thornton | 1 (1990-91) |
| 3 (1995-98) | Darcy Tucker | 8 (1999-2008) |
| 1 (2017-18) | Rinat Valiev | 1 (2015-16) |
| 1 (1920-21) | Cully Wilson | 2 (1919-21) |
| Montréal | GOALTENDERS (9) | Toronto |
|---|---|---|
| 3 (1940-43) 1 (1945-46) |
Paul Bibeault | 1 (1943-44) |
| 1 (1933-34) | Lorne Chabot | 5 (1928-33) |
| 7 (1926-33) 1 (1936-37) |
George Hainsworth | 4 (1933-37) |
| 8 (1973-81) | Michel Larocque | 3 (1980-83) |
| 1 (1962-63) | Cesare Maniago | 1 (1960-61) |
| 11 (1952-63) | Jacques Plante | 3 (1970-73) |
| 1 (2015-16) | Ben Scrivens | 2 (2011-13) |
| 2 (1972-74) | Wayne Thomas | 2 (1975-77) |
| 4 (1980-84) | Rick Wamsley | 2 (1991-93) |
| Montréal | HEAD COACHES (2) | Toronto |
|---|---|---|
| 4 (1988-92) | Pat Burns | 4 (1992-96) |
| 15 (1940-55) |
Dick Irvin | 9 (1931-40) |
Two Solitudes 