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For McCaskill, 2012 marks the fifth time she will be on a statewide ballot, having won twice as state auditor and once as Senator and having lost a gubernatorial race.
For Allen, this year is his fourth running statewide; his last race ended in the loss of the Senate seat he is now trying to reclaim.
Each politician's sole statewide loss was difficult to stomach.
In 2004, McCaskill lost 51 percent to 48 percent to Republican Matt Blunt, falling short of her longtime goal of being elected Missouri's first female governor. "I learned a lot from that loss," she told students Tuesday at her alma mater, the University of Missouri in Columbia.
Two years later, she put together the pieces to win her Senate seat, becoming the first woman elected to the Senate from Missouri.
While McCaskill was celebrating the night of Nov. 7, 2006, Allen lost 50 percent to 49 percent to Democrat Jim Webb in a race defined in part by their differences on the war in Iraq but also by a painful episode in which Allen referred to an Indian-American Webb aide as "macaca" and welcomed him "to America, and the real world of Virginia" at a campaign event the aide captured on videotape.
It's been six years since Allen's loss and he obviously hopes he can find a way to write another, more positive chapter for his political biography, even if his dreams of the presidency may be quashed.
For now, however, both are focused on creating the same kind of contrast for voters that Obama and Romney attempted to make in their convention speeches.
Allen, for instance, vowed to retirees at Leisure World in Leesburg, Va., that he was looking forward to "being the deciding vote to repeal Obamacare."
McCaskill said Democrats have a more difficult sell to the public when it comes to the Affordable Care Act but that it will eventually take hold as people see the benefits.
"The message on our side, is a little more complicated. ... Our side of the equation is complicated policy that doesn't lend itself to easy sound bites. Their side of the equation is, 'Don't trust the government,'" she said in Warrensburg.