Note: Technically the elections of John Adams & Thomas Jefferson in 1796/1800 would count here, but given how unusual elections were during the first 30 years of the republic, I didn't profile them as an election in the same fashion.
The Elections: 1824 & 1828
The Elections: 1836 & 1840
The Elections: 1888 & 1892
The Elections: 1896 & 1900
The Elections: 1952 & 1956
The Opponents: John Quincy Adams (Democratic-Republican/National Republican) & Andrew Jackson (Democratic-Republican/Democrat)
Who Won First?: John Quincy Adams
Who Won Second?: Andrew Jackson
The Story: The election of 1824 was one of the least democratic (small 'd') in history. Jackson won a plurality of both the popular & electoral vote, but due to Adams, Henry Clay, & William Crawford all running alongside him, he could not get the majority (it's worth noting that Adams would've been the electoral college victor were it not for the three-fifths compromise). Adams, with the help of Henry Clay, was able to work his way through the House of Representatives and get a quick victory due largely to the smaller states in New England giving him the edge over Jackson & Crawford. Jackson used Adams' appointment of Clay to be Secretary of State (then the most logical successor position to the White House) led him to call Adams corrupt. He'd spend four years doing this, with success when he beat Adams outright four years later (and Clay four years after that)...and in the process launched what would become the two-party system.
The Opponents: Martin Van Buren (Democrat) and William Henry Harrison (Whig)
Who Won First?: Martin van Buren
Who Won Second?: William Henry Harrison
The Story: In 1836, it was clear that the Whigs wanted to try a new tactic to take the election after eight years of Andrew Jackson & the Democratic Party being in charge, so in hopes of throwing the election to the House, they ran multiple candidates from across the country, thinking a favorite son approach might do the trick. It didn't work, though, with the best of the favorite sons (Harrison) being crushed by Van Buren, who became the third vice president to succeed their president (a feat that wouldn't happen for 152 more years after that). Four years later, the economy was in shambles, and while Van Buren kept the popular vote close, the electoral college was a blowout for Harrison, who would die just one month after taking office. Van Buren would spend much of the next four years trying to secure the nomination again, and when that didn't work, he ran as a third party candidate in 1848, likely costing Lewis Cass the White House against Zachary Taylor.
The Opponents: Benjamin Harrison (Republican) & Grover Cleveland (Democrat)
Who Won First?: Benjamin Harrison
Who Won Second?: Grover Cleveland
The Story: This is surely the election that Trump is most hoping to emulate, because it's the one that would be the closest corollary to next year. When the election of 1888 happened, Grover Cleveland was the incumbent president. Cleveland was unpopular with certain factions of the country due to his anti-tariff policies, as well as being critical of war pensions, but was very strong in the South, and it was a close election, with the popular vote being decided by less-than-a-point in Cleveland's favor. However, Harrison won due to Cleveland's popularity being concentrated in the South (and winning a tight race in New York), and so he won the White House. Four years later, Cleveland's stances on tariffs were more popular, and as he hung onto the South, he also took several northern states, including crucial New York, getting him a second, non-consecutive term. Four years later, Harrison was chatted over to make a third consecutive run, but refused in favor of William McKinley.
The Opponents: William McKinley (Republican) & William Jennings Bryan (Democrat)
Who Won First?: William McKinley
Who Won Second?: William McKinley
The Story: So far all of this has to have pleased Donald Trump. After all, the first three races featured a 50/50 split in terms of wins & losses. The last two matchups, though, were entirely one-sided. The first was the election of 1896, which was a slam dunk for McKinley largely due to the economic depression that had dogged much of Cleveland's second term in office. Bryan was also a unique politician, a populist and a famously loquacious statesman, far more into retail politicking than McKinley. McKinley was quite popular, and enjoyed a turnaround in the economy, which doomed Bryan in his reelection attempt four years later. McKinley, though, would end up something of a loser in that election as well-six months after his victory, he'd be assassinated and would be overshadowed in history by his successor, Teddy Roosevelt. Bryan would be his party's nominee a third time in 1908, losing that year to William Howard Taft, and eventually get into the White House under a different guise, as Woodrow Wilson's Secretary of State.
The Opponents: Dwight D. Eisenhower (Republican) & Adlai Stevenson II (Democrat)
Who Won First?: Dwight D. Eisenhower
Who Won Second?: Dwight D. Eisenhower
The Story: In 1952, Harry Truman was so wildly unpopular due to his handling of the Korean War & for not keeping the Cold War under control (Truman didn't even run for reelection even though he was constitutionally eligible), that it was certain the GOP would win no matter whom they nominated. It helped when they put up the hero of WWII, General Ike Eisenhower, who earned the moniker "I Like Ike." If Harrison/Cleveland was inspiration for Trump, Biden has to like this matchup. Four years later, Eisenhower's steady hand actually increased his margins against Stevenson, who lost even more states (though weirdly not Missouri, the only time in the 20th Century the Show Me State got a presidential election wrong). Stevenson would attempt in 1960 to get the nomination not by running, but through a draft, and in the process pissed off the Kennedy Brothers, denying him the Secretary of State position when JFK would become president (Stevenson had to settle for UN Ambassador).
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