Milward Simpson Republican John J. Hickey Democratic The 1958 Wyoming gubernatorial election 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.

Simpson attributed him defeat to his failure to win the traditional Republican Sheridan County.