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Penalty Minutes Multiple Winners: Red Horner (8); Gus Mortson and Dave Schultz (4); Bert Corbeau, Lou Fontinato and Tiger Williams (3); Matthew Barnaby, Billy Boucher, Carl Brewer, Red Dutton, Pat Egan, Bill Ezinicki, Joe Hall, Tim Hunter, Keith Magnuson, Chris Nilan, Jimmy Orlando and Rob Ray (2). | Year | | Min |
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| 1918 | Joe Hall, Mon | 60 | | 1919 | Joe Hall, Mon | 85 | | | | | | 1920 | Cully Wilson, Tor | 79 | | 1921 | Bert Corbeau, Mon | 86 | | 1922 | Sprague Cleghorn, Mon | 63 | | 1923 | Billy Boucher, Mon | 52 | | 1924 | Bert Corbeau, Tor | 55 | | 1925 | Billy Boucher, Mon | 92 | | 1926 | Bert Corbeau, Tor | 121 | | 1927 | Nels Stewart, Mon-M | 133 | | 1928 | Eddie Shore, Bos | 165 | | 1929 | Red Dutton, Mon-M | 139 | | | | | | 1930 | Joe Lamb, Ott | 119 | | 1931 | Harvey Rockburn, Det | 118 | | 1932 | Red Dutton, NYA | 107 | | 1933 | Red Horner, Tor | 144 | | 1934 | Red Horner, Tor | 146 | | 1935 | Red Horner, Tor | 125 | | 1936 | Red Horner, Tor | 167 | | 1937 | Red Horner, Tor | 124 | | 1938 | Red Horner, Tor | 82 | | 1939 | Red Horner, Tor | 85 | | | | | | 1940 | Red Horner, Tor | 87 | | 1941 | Jimmy Orlando, Det | 99 | | 1942 | Pat Egan, NYA | 124 | | 1943 | Jimmy Orlando, Det | 99 | | 1944 | Mike McMahon, Mon | 98 | | 1945 | Pat Egan, Bos | 86 | | 1946 | Jack Stewart, Det | 73 | | 1947 | Gus Mortson, Tor | 133 | | 1948 | Bill Barilko, Tor | 147 | | 1949 | Bill Ezinicki, Tor | 145 | | | | | | 1950 | Bill Ezinicki, Tor | 144 | | 1951 | Gus Mortson, Tor | 142 | | 1952 | Gus Kyle, Bos | 127 | | 1953 | Maurice Richard, Mon | 112 | | 1954 | Gus Mortson, Chi | 132 | | 1955 | Fern Flaman, Bos | 150 | | 1956 | Lou Fontinato, NYR | 202 | | 1957 | Gus Mortson, Chi | 147 | | 1958 | Lou Fontinato, NYR | 152 | | 1959 | Ted Lindsay, Chi | 184 | | | | | | 1960 | Carl Brewer, Tor | 150 | | 1961 | Pierre Pilote, Chi | 165 | | 1962 | Lou Fontinato, Mon | 167 | | 1963 | Howie Young, Det | 273 | | 1964 | Vic Hadfield, NYR | 151 | | 1965 | Carl Brewer, Tor | 177 | | 1966 | Reg Fleming, Bos-NYR | 166 | | 1967 | John Ferguson, Mon | 177 | | 1968 | Barclay Plager, St.L | 153 | | 1969 | Forbes Kennedy, Phi-Tor | 219 | | | | | | 1970 | Keith Magnuson, Chi | 213 | | 1971 | Keith Magnuson, Chi | 291 | | 1972 | Bryan Watson, Pit | 212 | | 1973 | Dave Schultz, Phi | 259 | | 1974 | Dave Schultz, Phi | 348 | | 1975 | Dave Schultz, Phi | 472 | | 1976 | Steve Durbano, Pit-KC | 370 | | 1977 | Tiger Williams, Tor | 338 | | 1978 | Dave Schultz, LA-Pit | 405 | | 1979 | Tiger Williams, Tor | 298 | | | | | | 1980 | Jimmy Mann, Win | 287 | | 1981 | Tiger Williams, Van | 343 | | 1982 | Paul Baxter, Pit | 409 | | 1983 | Randy Holt, Wash | 275 | | 1984 | Chris Nilan, Mon | 338 | | 1985 | Chris Nilan, Mon | 358 | | 1986 | Joey Kocur, Det | 377 | | 1987 | Tim Hunter, Calg | 361 | | 1988 | Bob Probert, Det | 398 | | 1989 | Tim Hunter, Calg | 375 | | | | | | 1990 | Basil McRae, Min | 351 | | 1991 | Rob Ray, Buf | 350 | | 1992 | Mike Peluso, Chi | 408 | | 1993 | Marty McSorley, LA | 399 | | 1994 | Tie Domi, Win | 347 | | 1995 | Enrico Ciccone, TB | 225 | | 1996 | Matthew Barnaby, Buf | 335 | | 1997 | Gino Odjick, Van | 371 | | 1998 | Donald Brashear, Van | 372 | | 1999 | Rob Ray, Buf | 261 | | | | | | 2000 | Denny Lambert, Atl | 219 | | 2001 | Matthew Barnaby, Pit-TB | 265 | | 2002 | Peter Worrell, Fla | 354 | | 2003 | Jody Shelley, Clb | 249 | | 2004 | Sean Avery, LA | 261 |
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