Cowboy Bob may refer to:
- Bob Bradley (wrestler) (also "Cowboy" Bob Bradley), retired American professional wrestler
- Bob Kelly (wrestler) (also "Cowboy" Bob Kelly; 1936–2014), American professional wrestler and booker
- Robert H. Macy (also "Cowboy Bob"; 1930–2011), Democratic District Attorney
- Bob Orton Jr. (also "Cowboy" Bob Orton; born 1950), American retired professional wrestler
- Cowboy Bob, a fictional character from the daily syndicated newspaper comic strip Dennis the Menace
- Peggy Jo Tallas, who was wanted by the FBI under this name when she robbed banks in disguise
This disambiguation page lists articles associated with the title Cowboy Bob.
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