LOST:
1824 to John Q. Adams

Crawford was again a leading candidate for the Democratic-Republican presidential nomination in 1824, but a massive stroke in 1823 ended his chances. The Democratic-Republican Party split apart that year, and one of the splinter groups nominated Crawford. Despite Crawford's improved health (and the support of former presidents Madison and Thomas Jefferson), he finished only third, behind John Quincy Adams and Andrew Jackson.

This election is notable for being the first (and, as of 2005, only) time since the passage of the Twelfth Amendment that the presidential election was thrown into the House of Representatives. It was also the first (and only) time that the president did not win the electoral vote. (It is also often said to be the first election in which the president did not win the popular vote. This is hard to determine, insofar as a quarter of the states did not conduct a popular vote, instead having the state legislature choose their electors.)