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Tom Glavine has won two Cy Young Awards, one in 1991, and the other in 1998.
Koufax won three Cy Young Awards, 1963, 1965 and 1966. Starting in 1956 when the Cy Young Award was created, only one award was presented for the entire Major Leagues. After 1966, both the American and National Leagues presented Cy Young Awards.
4 Cy Young Awards. Steven Norman Carlton (born December 22, 1944), nicknamed "Lefty", is a former Major League Baseball left-handed pitcher. He pitched from 1965-1988 for six different teams in his career, but it is his time with the Philadelphia Phillies where he received his greatest acclaim as a professional and won four Cy Young Awards.