"Just got a front row seat to watch @HillaryClinton overwhelm @realDonaldTrump at the 'Humbling at Hofstra' on Monday. It Is On!" Cuban tweeted.
The two billionaires have feuded regularly in recent years. At a July campaign stop for Clinton, Cuban called Trump "bats--- crazy."
On Sunday, he taunted Trump on Twitter: "Donald. Remember when you told me on the phone we were 'Bobbsie Twins' and I laughed?"
And Trump tweeted that he might invite Flowers - first in a tweet that misspelled her name as "Jennifer," which was deleted within minutes, quickly followed by a repeat. Both tweets also mentioned Cuban's "Apprentice"-like TV show, which was canceled in 2004: "If dopey Mark Cuban of failed Benefactor fame wants to sit in the front row, perhaps I will put Gennifer Flowers right alongside of him!"
Clinton spokeswoman Jennifer Palmieri responded to the news Sunday: "Hillary Clinton plans on using the debate to discuss the issues that make a difference in people's lives. It's not surprising that Donald Trump has chosen a different path."
It also remains to be seen whether the Commission on Presidential Debates, which organises the debates, would allow either Cuban or Flowers to sit in the front row. Commission co-chairman Frank Fahrenkopf told CNN on Sunday, before the news about Flowers, that attempts to distract the candidates with guests will be discouraged.
"We are going to frown upon - I will tell you this right now - whether or not a Republican or Democrat or anyone else attempts by use of tickets in placing people in a front row or not to try to impact the debate. It is wrong," Fahrenkopf said. "We would frown upon Mr. Cuban being in the front row if his purpose is to somehow disrupt the debate; likewise, if Mr. Trump was going to put someone in the front row to try and impact things."
Flowers said during Bill Clinton's 1992 presidential campaign that the two of them had engaged in an affair over a dozen years. The allegation, which Clinton denied at the time, threatened to ruin his campaign.
In 1998, Bill Clinton acknowledged under oath having a sexual encounter with Flowers, though he disputed details of her account.