The UFC returns to Chicago on Saturday, marking the first time the Octagon has landed in “The Windy City” since 2019. Atop the UFC 319 fight card is a middleweight title showdown between champion Dricus du Plessis and elite challenger Khamzat Chimaev.
Du Plessis has defied expectations since joining the UFC, proving himself against the best 185 pounds has to offer. He defeated former champ Robert Whittaker in a title eliminator, defeated Sean Strickland to win the title and successfully defended the title against another former champ in Israel Adesanya.
Chimaev entered the UFC as a force of nature, running through opponents in short order while putting up stunning striking differential numbers. After years of speculation over when Chimaev’s chance to become champion would come, he finally gets his crack on Saturday night.
In the co-main event, former Bellator star Aaron Pico makes his UFC debut against undefeated Lerone Murphy.
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With a massive title fight in the main event and intriguing fights up and down the card, there’s sure to be plenty of action at sportsbooks around the country and we’re here to give our picks for the best bets for each of the five UFC 319 main card fights.
After a slightly disappointing 2-3 result for our best bets for UFC 317 (we took UFC 318 off), our 2025 record sits at 18-15. We’ll look to get our roll going again on Saturday, with our only rule remaining that all bets must be at odds of -250 or better. Let’s take a look at this week’s picks with odds via DraftKings.
Tim Elliott vs. Kai Asakura
Kai Asakura via KO/TKO/DQ (+140)
Alexandre Pantoja and the UFC flyweight championship were a step too far for Asakura in his most recent outing, with Pantoja securing a second-round choke to finish their UFC 310 fight. That fight was also Asakura’s Octagon debut, having been a star in Rizin prior to signing with the UFC. By contrast, Elliott is a longtime UFC veteran. Saturday will mark his 20th trip to the Octagon and 35th professional bout. Elliott can be a tricky opponent, with an unorthodox striking style and a solid ground game. Asakura is the far more explosive striker, with fantastic timing and good power. Asakura is a heavy favorite entering the fight, and as long as he doesn’t get smothered by Elliott’s wrestling, a stoppage is the most likely way this fight ends.
Jared Cannonier vs. Michael Page
Michael Page via decision (+100)
This is a tricky fight, and there’s a nagging part of my brain saying that under 2.5 rounds at +210 is the play. However, Page isn’t the wrecking ball finisher he was earlier in his career. This is a result of Page settling into a style where he more safely uses his speed and length to fluster opponents while picking them apart rather than going for the killshot from the opening bell. Cannonier is an experienced fighter at a high level, but he’s also 41 and age and miles are starting to show a bit more in his performances. Unless Cannonier can routinely close the distance (a difficult task against Page), this is likely to be a long night of Cannonier chasing a ghost while he gets tagged by Page’s in-and-out style of striking. In a three-round fight, that should lead to a Page decision victory.
Geoff Neal vs. Carlos Prates
Carlos Prates moneyline (-250)
This line sneaks in at the top end of our acceptable odds and we’ll take it. Prates via KO is listed as the most likely outcome at +110, but Neal has not been stopped in his UFC career (12 fights), so we can hedge our bets a little here. Prates tore through his first four UFC opponents, scoring knockouts in each fight before losing to Ian Machado Garry in his most recent outing. In Neal, Prates faces an experienced opponent who has enough tricks up his sleeve to make this a potential trap fight. We’re going to bet on the talent and explosiveness of Prates to win out here, but leaving the decision on the table rather than betting on the knockout.
Lerone Murphy vs. Aaron Pico
Aaron Pico moneyline (-180)
We’ve seen former Bellator stars come to the UFC and stumble recently. Patricio Pitbull lost his first UFC fight and Patchy Mix turned in an absolute dude in his debut. Pico is trying to shake that trend in a co-main event fight with Murphy. Pico was an absolute blue-chip prospect when he entered MMA, but lost his debut in 24 seconds and started his career at 4-3. He then went on to win nine of his next 10 fights, with the lone loss coming due to a shoulder injury suffered in the fight. Pico is still young at just 28 and has every tool to be the fighter he was expected to be when he first stepped into the cage. Murphy is undefeated in 17 fights, including nine bouts in the UFC. Pico has a strong edge in wrestling and has sharp boxing, he is also a better finisher, with only two of 13 wins by decision compared to nine of 16 for Murphy. Once again, we’re leaning toward the more talented fighter with more avenues to victory in this one and expecting a Pico win in his Octagon debut.
Dricus du Plessis vs. Khamzat Chimaev
Dricus du Plessis moneyline (+205)
Going back through past CBS Sports predictions, I don’t believe I’ve ever picked against du Plessis. As an early adopter of “Stillknocks,” I’m not changing my ways until given reason to do so. Chimaev is an absolute terror in the first round. His wrestling and dominant top game are elite and he runs through opponents. Unless, that is, those opponents can drag him into the second and third rounds. Chimaev struggled at times in winning decisions against Gilbert Burns and Kamaru Usman, looking visibly fatigued from the second round onward against both. Chimaev was able to dig deep enough against those men to grind out the decision, but those cardio issues could be a massive issue against du Plessis and his deep gas tank. Everything about du Plessis is awkward. He fights all wrong but does so successfully, in part because he just keeps coming while his opponents start to fade. If du Plessis can get through the first round, his chances to win rise dramatically. If he gets through the second, those chances skyrocket. This is a five-round fight and that’s du Plessis’ world, and I think he’s too awkward and stubborn to get ran over just minutes into the fight.
Who wins UFC 319: Du Plessis vs. Chimaev, and how exactly does the fight end? Visit SportsLine now to get detailed picks and analysis from the incomparable expert who is up over $1,500 on his UFC main-card picks, and find out.
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