Derek Brunson smiles and looks off into the distance. He’s thinking about all of the world-class opponents he has competed against during his nine-year career.

In just his third UFC fight, Brunson took on 2000 Olympic wrestling silver medalist Yoel Romero. Half of his 10 most recent fights have come against opponents who were champions in either the UFC or Strikeforce. When it comes to strength of schedule, there isn’t a 185-pound fighter who has navigated more of a minefield en route to contendership.

“I’ve done a lot in the middleweight division,” Brunson told ESPN. “The only thing I haven’t done was be a champion. Some people had easier roads to being the champion.”

That title shot is within sight now. Brunson has won four straight fights going into a big main event against Darren Till at UFC Fight Night on Saturday in Las Vegas (1:30 p.m., ESPN+). The winner will be right there in the mix for a chance at the belt.

Former champion Robert Whittaker is likely next up as a challenger for champion Israel Adesanya. But if Brunson can beat Till, he and Jared Cannonier are the two most likely to be in the title shot conversation next year. ESPN has Brunson ranked No. 7 and Till ranked No. 8 at middleweight. A spectacular win, Brunson feels, would put him in “prime” position.

“I think for sure if I go out here and finish this guy impressively, it’s going to be really hard not to give me the next title shot after Whittaker and Adesanya,” Brunson said.

Brunson (22-7), of course, has already fought both Adesanya and Whittaker already. Because the 37-year-old, who fights out of Florida’s Sanford MMA, has fought a who’s who of the top middleweights in the world over his 18 UFC fights.

ESPN asked Brunson to rank the top five middleweight fighters he has been in the Octagon with over the last near-decade.

1. Anderson Silva (beat Brunson via unanimous decision at UFC 208 on Feb. 11, 2017)

This fight is one that sticks in Brunson’s craw to this today. He — and many, many others — felt like he should have been the rightful winner. According to MMADecisions.com, 20 of the 24 journalists who scored the bout had it for Brunson. Eight of those had Brunson winning all three rounds. Brunson outlanded Silva 118-54 in total strikes and 54-43 in significant strikes.

However, Brunson picks Silva as his top middleweight opponent because of what “The Spider” did in his career. The Brazilian knockout artist held the UFC’s 185-pound title over seven years and still owns the record for the longest winning streak in promotion history (16 fights). Silva lost seven of his last nine UFC fights before being released last year. But Brunson said it has to be considered that most of those defeats were when Silva was over 40 years old and past his prime.

“Let’s say Khabib [Nurmagomedov] fought until he was 46,” Brunson said. “You think he would be undefeated? Probably not. He’s probably going to lose four or five towards the end of his career. That’s what every great does.”

2. Israel Adesanya (beat Brunson via TKO at UFC 230 on Nov. 3, 2018)

Adesanya caught Brunson with just nine seconds left in the first round. Brunson said he doesn’t feel like Adesanya was schooling him at all during that fight, but he got overzealous trying to go in for a takedown and Adesanya capitalized on that. Brunson has maintained that he is a much different fighter now than he was then, and there is definite proof in the pudding looking at his current winning streak. Adesanya, Brunson noted, hasn’t called him out much despite his four straight victories. Adesanya has mentioned Till, he’s said he wants to fight Cannonier, but Brunson has not been mentioned.

“Maybe he feels I’m one of his biggest threats,” Brunson said. “He’s seen me turn it around, being a better version of myself, improving some things on the feet, not rushing in for the takedown.”

With that being said, Brunson said he respects what Adesanya has done and believes he can pass Silva in these rankings eventually. Adesanya is 10-0 at middleweight in the UFC and has three successful title defenses.

“Izzy still has time to be No. 1,” Brunson said.

3. Robert Whittaker (beat Brunson via TKO at UFC Fight Night on Nov. 27, 2016)

Brunson and Whittaker got into a wild slugfest in the first round of their main event fight. Brunson rocked Whittaker and tried to blitz in to inflict more damage, but Whittaker landed a huge left hand that wobbled him. Seconds later, Whittaker crushed Brunson with a right head kick that led to the finish. Both fighters won a $50,000 bonus for Fight of the Night.

Whittaker is the most likely next contender for Adesanya’s title. Adesanya knocked out Whittaker to win the undisputed title at UFC 243 in October 2019. Since then, Whittaker has looked very strong, winning three straight. Brunson believes the outcome could be different if Whittaker fights Adesanya once again.

“I think he can switch it up,” Brunson said. “I think he can make some adjustments and make the fight more interesting — and closer, for sure.”

4. Yoel Romero (beat Brunson via TKO at UFC Fight Night on Jan. 15, 2014)

Of his five losses in the UFC, this one might bother Brunson the most. Brunson did very well over the first two rounds, which most thought he won. In the third round, he gassed out and Romero blasted him with left hooks and uppercuts before finishing him on the ground. That was a “super green” Brunson’s third fight in the UFC, and he said he had no idea about nutrition, hydration and cutting weight at the time.

What makes it even worse is that Brunson believes that had he won, he would have been close to a title shot against then-champion Chris Weidman, with whom Brunson believes he would have matched up very well. Brunson would have been 3-0 in the UFC if he held on and beat Romero, who went on to be a top contender for years.

“That’s probably one of my tougher losses throughout my whole MMA career,” Brunson said.

5. Derek Brunson (13-5 UFC record)

Well, yes, Brunson has been in the Octagon with himself — and he puts himself in this spot over the likes of Ronaldo “Jacare” Souza, Lyoto Machida and Uriah Hall, his other top opponents. Getting older and more mature, plus the move to Sanford MMA with coach Henri Hooft, has made Brunson better than he has ever been, he said. Brunson believes he’s “getting closer to the best version of myself.”

“I still have room to get better,” he said.

He has a chance to show that against Till on Saturday. A huge finish or pristine performance in that one and we could be talking about Brunson finally getting the title shot that has eluded him over the last nine years.

“My vision is to win this fight, get a title shot, win the title, defend it a couple times and then just be done,” Brunson said. “There’s really no plan on being done [now]. But when I achieve everything I want to achieve, there’s almost nothing else to achieve. Leave with a sound mind, really smart, not much damage and move on to the next page.”

If that all happens, it would be quite the journey. And few have had it tougher in the UFC.

“There’s no denying it,” Brunson said. “If you had some metrics where you had a strength of schedule, I’m pretty sure I’m going to be up there.”