Twice, once in 1968 and again when he tied Mike Cuellar for the Award in 1969.
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As of the 2008 season, no Cincinnati pitcher has won the Cy Young Award.
He never won the Award
He won the Award 3 times, 1963, 1965 and 1966.
He won the Award 3 times, 1969, 1973 and 1975.
He won the Award 4 times, 1972, 1977, 1980 and 1982