In 1824 John Quincy Adams, thanks to the Electoral College, became the President of the United States. Four years later, the popular vote winner in that election, Andrew Jackson won the first of two presidential terms.
In 1876 Rutherford B Hayes, in a questionable electoral college tally, beat popular vote winner Samuel Tllden for the Presidency. Tilden probably would have run again in 1880 but ill health prevented him. He would die in 1886.
In 1888 Benjamin Harrison achieved an electoral college victory over incumbent President and popular vote winner Grover Cleveland. Four years later, Cleveland would become the first President to serve two non-consecutive four-year terms.
In 2000, Vice President Al Gore won the popular vote over George W, Bush but a poorly constructed butterfly ballot in Palm Beach (where voters erroneously voted for the Pre Trump Pat Buchanan) and a Republican-friendly Supreme Court tipped the electoral college to George W. Bush. Criticized for the campaign he ran in 2000 (where he did not emphasize the peace and prosperity of the Clinton/Gore Administration), Gore decided not to run in 2004.