TLDR
- Ben Askren and Jorge Masvidal discussed their UFC 239 knockout on Masvidal’s Death Row MMA show
- Masvidal knocked out Askren with a flying knee in just five seconds in July 2019
- Askren said he never saw the angle coming because Masvidal used a unique jumping trajectory instead of coming straight up
- Masvidal studied Askren’s fights and planned to trigger his takedown instinct by closing distance quickly
- The knockout ended Askren’s undefeated record and launched Masvidal to UFC title opportunities
Sources: mmafighting.com | timesofindia.indiatimes.com
Ben Askren and Jorge Masvidal sat down together recently to discuss the flying knee knockout that connected them forever in MMA history. The former rivals appeared on Masvidal’s Death Row MMA show to break down the UFC 239 finish from July 2019.
The knockout happened just five seconds into their fight. Masvidal’s flying knee left Askren unconscious on the mat in one of the fastest finishes in UFC history.
Jorge Masvidal and Ben Askren finally sat down to talk about the flying knee KO 🤯
“I looked at everything you did. I was watching you since your sophomore year in college. That’s how much I knew about you… I noticed something in a lot of your fights.”
(via @deathrow_mma) pic.twitter.com/X7i1PWcj33
— Happy Punch (@HappyPunch) October 9, 2026
Askren had never been knocked out before that moment. The two-time NCAA Division-I freestyle wrestling champion went undefeated in his first 21 professional fights, winning championships in both Bellator and ONE Championship.
Why Askren Never Saw It Coming
Askren explained that Masvidal’s flying knee came from a different angle than he had ever seen before. Most flying knees come straight up when fighters are close together.
“You did more of a jumping trajectory,” Askren said. “I completely misjudge your trajectory because I’d never, ever seen anyone do it like that before.”
Askren said his brain couldn’t predict where the strike was coming from. He had probably never been hit with a flying knee in his entire career before that night.
“You weren’t coming from straight up, you were coming from an angle, and so my brain obviously misread it and then you’re done,” Askren explained.
Masvidal studied Askren’s fighting style carefully before the match. He noticed that Askren would shoot for takedowns or clinch whenever he felt uncomfortable at striking range.
“I would watch all your fights,” Masvidal said. “So I just noticed in a lot of your fights, if all of a sudden you were in a range that you didn’t like, you would shoot or you would find a way to clinch.”
Masvidal’s Calculated Risk
Masvidal wanted to avoid defending Askren’s wrestling at all costs. He knew Askren had been in wrestling positions thousands of times and would have the advantage there.
The plan was to make Askren think a punch was coming from close range. Masvidal hoped this would trigger Askren’s instinct to shoot for a takedown.
“If I make it seem like I’m going to punch and close the distance, I think he’ll give me what I want and I can anticipate the shot,” Masvidal said. “I wanted you first to feel that I’m close. I wanted you to feel that I’m in right hand range and then bam.”
Askren confirmed that Masvidal’s strategy worked perfectly. When he saw Masvidal getting close, his immediate reaction was to drop and go for a takedown.
“When I saw you, to your point, I probably said, ‘Shit, he’s getting close,’ drop, drop, takedown,” Askren said. “I hadn’t seen the flying knee so that was where I got myself in trouble.”
The knockout launched Masvidal to new levels of fame. He earned two UFC title opportunities after the win and became one of the biggest stars in the sport.
Askren fought one more time after the loss before retiring from MMA. He later moved on to other ventures outside of fighting.
Masvidal has since retired from UFC competition after losing to Gilbert Burns in 2023. He now runs his own promotion called Gamebred FC.
