1789 Virginia's 5th congressional district election

The first election for Virginia's 5th congressional district took place on February 2, 1789, for a two-year term to commence on March 4 of that year. In a race that turned on the candidates' positions on the need for amendments (the Bill of Rights) to the recently ratified U.S. Constitution, James Madison defeated James Monroe for a place in the House of Representatives of the First Congress. It is the only congressional election in U.S. history in which two future presidents opposed each other.

The race came about when former governor Patrick Henry and other Anti-Federalists in the Virginia General Assembly, who had opposed the state's ratification of the Constitution, sought to defeat Madison, who had been a strong advocate for ratification, and who wanted to become a member of the new House of Representatives; they had already defeated him in the legislative election to choose Virginia's first U.S. senators. They put forward Monroe, a young but experienced politician who was a war hero wounded at the 1776 Battle of Trenton, as a candidate for the seat. Monroe did not seek the contest, but once drafted campaigned vigorously. Despite bitterly cold weather, the two candidates debated outdoors; traveling after one such meeting, Madison suffered frostbite on his face.

Although Madison had earlier stated that amendments to the Constitution were not necessary, during the campaign he took the position that they were, but should be proposed by Congress, rather than by an Article V Convention that Anti-Federalists such as Monroe and Henry supported. Madison won the election comfortably, to the satisfaction of his supporters such as President-elect George Washington. The race did not affect Madison's friendship with Monroe, who was elected to the Senate in 1790, and who would serve as Madison's Secretary of State and succeed him as president in 1817.