Jairzinho Rozenstruik punches Alistair Overeem during their main event fight at UFC Washington. Credit: Jeff Bottari/Zuffa LLC via Getty Images

A heavyweight showdown six years ago today proved that it’s never too late to have your lip torn off in a fight…

The UFC was in Washington D.C. on this day, December 7, in 2019. A number of notable names were in action, including former welterweight title challenger Thiago Alves, then-future featherweight contender Bryce Mitchell, and bantamweight striker Song Yadong.

The main focus at Capital One Arena was on the heavyweight division, with the legendary Alistair Overeem featuring in his fifth UFC main event at the time.

The Dutch powerhouse entered his fight with Jairzinho Rozenstruik riding a two-fight winning streak, having recorded consecutive knockouts against Sergei Pavlovich and Aleksei Oleinik.

But Overeem’s push back toward the heavyweight title was stopped in violent fashion…

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Which UFC fighter suffered the worst cut in history? 🩸

The likes of Alistair Overeem, Gregory Rodrigues, and Irene Aldana all suffered some of the most memorably gruesome gashes.

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Jairzinho Rozenstruik’s KO punch tore Alistair Overeem’s lip open in brutal UFC main event finish

Rozenstruik earned his maiden UFC main event after a 3-0 start in the promotion that included a 29-second KO against former heavyweight champion Andrei Arlovski. But through 24 minutes at UFC Washington, Overeem looked to be a hurdle too tall for the Surinamese powerhouse.

The former Strikeforce heavyweight champion had pulled ahead on all three scorecards, leading 39-37 on two of them and 40-36 on the other as the pair entered the fifth round.

But as the final seconds ticked down, ‘Bigi Boy’ finally found a home for his renowned power shot.

Rozenstruik finished Overeem with four seconds left, connecting with a frightening right hand that sat ‘The Reem’ down against the fence.

The Dutch veteran was quick to return to his feet, but his stumbling convinced referee Dan Miragliotta to wave the fight off.

The superficial damage that Overeem had suffered soon became clear, with his lip being completely torn open on one side. The gruesome injury was widely described as one of the worst ever seen inside the Octagon.

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Photo by Jeff Bottari/Zuffa LLC via Getty Images

Dana White defends his comments after the most recent UFC heavyweight title fight

Fast forward six years and neither Overeem nor Rozenstruik remain in the UFC heavyweight division.

A new crop of behemoths have risen through the ranks and cemented themselves as this generation’s heavyweight stars, but their weight class has been going through a difficult period.

After Jon Jones was accused of holding the title hostage by refusing to fight then-interim champ Tom Aspinall, the Englishman’s undisputed reign eventually got underway with a less than ideal first defense this past October.

Ciryl Gane’s eye poke against Aspinall resulted in a no-contest at UFC 321, and some of the comments in the aftermath have left the champ unhappy.

After Aspinall publicly called out Dana White’s remarks about his injury, the promotion’s president responded during his post-fight press conference at Saturday’s UFC 323 pay-per-view.

“I get it. I don’t remember exactly what I said…that I think his eyes were okay?” White said.

Photo by Jeff Bottari/Zuffa LLC

“Here’s the thing, I know Tom said I haven’t even talked to him, but we have people all over him right now, checking up on him, making sure he’s good, (asking) if he needs any help or a specialist.

“I am no doctor. I am just saying what I’ve heard,” he continued. “It wasn’t said in a way, ‘Oh, I think he’s fine!’ I said, ‘I think Tom’s eyes are good, he’s gonna take some time, heal…’

“I wasn’t saying anything negative toward him. I think that things can be taken out of context, or he didn’t see what I said.

“Never once did I say anything negative about him in a derogatory way.”