The Wyoming gubernatorial election of 1958 took place on November 4, 1958. Incumbent Republican Governor Milward Simpson ran for re-election to a second term. He was challenged by John J. Hickey, the former U.S. Attorney for the District of Wyoming and the Democratic nominee. Following a close campaign, Hickey narrowly defeated Simpson for re-election, winning just a narrow plurality because of a third-party candidate in the race. In an irony, just four years later, in the 1962 special U.S. Senate election, Simpson would defeat Hickey, avenging his loss in the gubernatorial election.