After years of buildup, Tyron Woodley and Colby Covington's rivalry eventually culminated with a UFC Fight Night main event in 2020, which Covington won with a late stoppage.

Covington has made enemies out of essentially the entire UFC welterweight division throughout his 22-fight career. A former member of American Top Team (ATT), "Chaos" even crossed paths with several former teammates, including Woodley. However, his time near the top of the division is likely over. Covington is just 2-4 over his past six fights after a one-sided stoppage loss to Joaquin Buckley at UFC Tampa. On Wednesday's "The Ariel Helwani Show," former UFC welterweight champion Woodley took a not-so-friendly trip down memory lane to reflect on his days in the gym with a young Covington.

"I don't want to rain on his parade, but the parade is kind of over with," Woodley said. "I think he disrespected the division. I think he disrespected other fighters by just picking and choosing his fights. I had defended the belt several times while he had an interim belt, and then now he comes and fights me when he thinks I'm down and out?

"Colby used to come in [the gym] — we used to laugh at him. I remember being at Dan Lambert's house. No bulls**t. It was me, Hector Lombard, Robbie Lawler, Thiago Alves, Ben Saunders. It was like a welterweight poker night at Dan Lambert's house. It was really fly, to be honest. We watched the fights, and I don't think Colby was there, but we were all laughing at how Colby was just so cap. He was going and telling other people how we were all scared to train with him, how he can't get no good work here. He was talking to these other teams, like Alpha Male or whatever about that.

"Then we all made a bet, like an inside bet," he continued. "If he can last one round with any of us who are trying to really put it on him, we'll all give him a $100,000. It was something ridiculous. That's how [confident we were] at that time."

Covington was infamously closest with fellow multiple-time UFC title challenger Jorge Masvidal at ATT before his departure. The duo once labeled each other as best friends. Woodley wasn't as close to Covington as Masvidal was, but he said he tried to treat Covington better than most.

Before Woodley became a UFC champion, a 2014 matchup against Rory MacDonald required some pressure-wrestler aid from Covington in camp. Woodley has always been touted for his game-planning, and this appeared to be the perfect solution to MacDonald. However, it didn't quite work as hoped.

"I brought him into St. Louis, I paid him, I put him in this nice place to stay," Woodley said of Covington. "I paid for all his food. I took him to the gun range, I set him up with chicks. Like, I did everything. Boxing private lessons, jiu-jitsu private lessons, strength and conditioning private lessons on top of paying him. Nobody was doing that for their training partners. I take care of my training partners. But he was just always running. He ran from me the whole training camp. He literally didn't want to work out. We doing wrestling drills, and you're looking around like, 'Who the hell else will I want to f**king help me wrestle besides you? That's why you're here.'

"I was fighting Rory MacDonald. I had him come in there because I knew [MacDonald would pressure me] — and he did actually, he did pressure my ass too, didn't he? I figured Rory would try to pressure me and push me against the cage, which he did. But Colby came in camp and just ran from me, and he just would do stupid sh**. I'll be choking him out and I would have to make the choice, do I keep choking and put him asleep? Do I break his arm? And then I'm like, I'm not going to be a dick. Then he'll pop up like he got out. Colby, dude. Stop. It's a whole movie in itself."

Ultimately, Covington got the last laugh in his saga with Woodley. The eventual collision was largely a patented Covington performance, as he grinded out Woodley en route to a fifth-round stoppage when Woodley suffered a rib injury. Woodley fought once more in the UFC after that before parting ways.

Covington has lost three of his past four fights since then. Despite Covington's continuously growing brash, outspoken character at the time, Woodley put up with it in the gym and remembers the straw that broke the camel's back.

"His act is trash. It was funny for a little bit when we were bored, when Jon [Jones] was on a hiatus, Ronda [Rousey] wasn't fighting, Conor [McGregor] was out," Woodley said. "We listened to Colby because he just came in. But in reality, I used to torture Colby. He never won a moment of anything, not even a minute. He never won a moment or any exchange one time. I think he left early acting like his foot was hurt in the training camp.

"I told Colby the last day that he trained with me, I said, 'Colby, you're a dick.' And I said, 'Today, if you act like you're getting out of an armbar or if you don't submit to a choke or if you get mad that I took you down and have an attitude — and I'm a f**king two-time All-American Hall of Fame wrestler, like I'm not supposed to take you down? — if you run from me, I'm going to break your f**king arm today. I'm going to choke you out. I'm going to knock you out. If you run from me and you run off the mat like you've been doing all camp, I'm going to follow you on the carpet and I'm going to commence to beating your ass. We got that clear?' He said, 'Yeah,' and we sparred — and he left the next day."

Woodley, 42, is set to make an expected MMA return in April 2025 after recently signing with the new Global Fight League team-based MMA promotion.