Roger Clemens has enough Cy Young Awards to fill a room. His seven awards are the record. He won Cys with Boston, Toronto, the New York Yankees and Houston, the first coming in 1986 and the last in 2004. If re-voting today, the 2004 award probably would go to Randy Johnson but Clemens likely would add another as his case for the 1990 award, when he finished in second place, is strong.
Randy Johnson is one of only two pitchers to win four consecutive Cy Young Awards (1999-2002). Before that, he earned the Cy with Seattle in 1995. He may have deserved at least one more in 2004.
Steve Carlton and Greg Maddux each won four times, Maddux being the first 4-peat from 1992-1995. Sandy Koufax won in 1963, ’65 and ’66 before retiring at 30, possibly with another Cy stored in his arthritic left arm.
The complete least of multiple Cy winners:
- Roger Clemens (7) – 1986, 1987, 1991, 1997, 1998, 2001, 2004
- Randy Johnson (5) – 1995, 1999, 2000, 2001, 2002
- Steve Carlton (4) – 1972, 1977, 1980, 1982
- Greg Maddux (4) – 1992, 1993, 1994, 1995
- Sandy Koufax (3) – 1963, 1965, 1966
- Tom Seaver (3) – 1969, 1973, 1975
- Jim Palmer (3) – 1973, 1975, 1976
- Pedro Martínez (3) – 1997, 1999, 2000
- Clayton Kershaw (3) – 2011, 2013, 2014
- Max Scherzer (3) – 2013, 2016, 2017
- Bob Gibson (2) – 1968, 1970
- Denny McLain (2) – 1968, 1969
- Gaylord Perry (2) – 1972, 1978
- Bret Saberhagen (2) – 1985, 1989
- Tom Glavine (2) – 1991, 1998
- Roy Halladay (2) – 2003, 2010
- Johan Santana (2) – 2004, 2006
- Tim Lincecum (2) – 2008, 2009
- Justin Verlander (2) – 2011, 2019
- Corey Kluber (2) – 2014, 2017
- Jacob deGrom (2) – 2018, 2019
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