This doesn't fully fit the bill but is an interesting example nonetheless. Remember that the two-term limit wasn't actually enshrined in the constitution until the 22nd Amendment was passed in 1951 after Franklin D. Roosevelt was elected a total of four times between 1932 and 1944. It was only considered good form prior to said amendment in part because Washington had proposed and set the precedent. Thus, this case from the first half of the 20th century should qualify to a certain extent nonetheless.
The 26th President was Theodore Roosevelt who was elected on a Republican Party ticket. Initially elected as Vice President in 1900 he ascended to the Presidency upon his predecessor's assassination in 1901. He was re-elected on a Republican ticket in 1904. In 1908, he did not stand for re-election, instead supporting Taft as his successor.
During Taft's term as president Roosevelt became increasingly unhappy with Taft's administration. This culminated in Roosevelt contesting the nomination again in 1912, hoping to win a third term as president on the Republican ticket. Roosevelt won a plurality of delegates in primary elections; however, at the time not all states held primaries and the majority of delegates from these states went to Taft. Ultimately, the RNC chose Taft as their candidate for the 1912 presidential election.
Roosevelt was not satisfied and instead set up his own party, the Progressive (Bull Moose) Party to contest the election. He was mildly successful, winning second place in the popular vote and the Electoral College over Taft. However, the Democratic candidate Wilson secured a plurality of the popular vote and a landslide Electoral College victory, probably due to the Republican vote being split between Taft and Roosevelt. A crude analysis suggests the election would have gone the other way with only one candidate on the Republican side.