Their first fight was fireworks, and their efforts to put together a rematch turned out to be fruitless, but Dillian Whyte still hopes a second professional duel with Anthony Joshua is in the offing for both men.
Whyte (31-3, 21 KOs) actually fought Joshua (28-4, 25 KOs) for the very first time in 2009 at the age of 20 in what was his debut amateur bout, winning a unanimous decision.
When their pair renewed their rivalry six years later in December 2015, Joshua was on the road to superstardom and months away from his crowning moment against Charles Martin at the O2 Arena.
Whyte did his best to derail AJ's plans, stunning the Watford fighter with a left hook in the second round. But the Body Snatcher ran out of steam, and after a lot of back-and-forth action, he was brutally knocked out in the seventh stanza.
Joshua and Whyte stuck to their individual paths after that, the former becoming a two-time unified world heavyweight champion, beating the likes of Joseph Parker (35-3, 23 KOs), Wladimir Klitschko, Alexander Povetkin and Andy Ruiz Jr (35-2-1, 22 KOs) in a rematch.
Whyte, on the other hand, became somewhat of a pay-per-view attraction himself, headlining big UK fight nights against Parker, Derek Chisora (36-13, 23 KOs), Povetkin and Tyson Fury (34-2-1, 24 KOs).
In 2023, Joshua and Whyte were supposed to fight for a second time in the paid ranks, with both men on the comeback trail after defeats to Oleksandr Usyk (23-0, 14 KOs) and Fury respectively.
But their fight was cancelled after Whyte returned 'adverse analytical findings' in a pre-fight test by the Voluntary Anti-Doping Association (VADA).
Whyte has since been cleared to resume his career after it was confirmed the positive drugs test was caused by a contaminated supplement, and has picked up wins against Christian Hammer and Ebenezer Tetteh.
He's now set to fight Joe Joyce (16-3, 15 KOs) on April 5th at Manchester's Co-Op Live Arena in his first big headline fight since 2022. The card will be streamed on DAZN and promoted by Queensberry.
But Whyte still believes an eventual rematch with Joshua is on the cards.
Whyte told The Ring's Louis Hart: "I think even after we finish boxing, [the fight] will always be there.
"We just have that chemistry and connection. I know from sources he wants to fight me and I want to fight him as well.
"It's one of those things where it's always going to be a good fight. The same with Derek Chisora, it will always be a good fight. So let's see."
Joshua's next fight plans are still to be hashed out following his knockout defeat to Daniel Dubois last September.
With a Tyson Fury rematch not looking likely in the immediate future, Joshua will angle for a shot at the winner of Daniel Dubois-Joseph Parker on Feb. 22, but he could also struggle at the negotiating table there too.
Should Whyte beat Joyce in April, a summer bout between the duo may make the most sense both stylistically, like Whyte claims, and financially.