UFC 299 predictions

Sean O’Malley is poised to take his stardom to another level. But there’s a lot of work to be done.

In the main event of UFC 299 on Saturday, O’Malley can kill multiple birds with one stone. His rematch with Marlon Vera marks his first defense of the bantamweight title, a chance to avenge the lone loss of his career, and a statement performance that could cement him as the kind of marquee combat sports act that can call his shots. Should he defeat “Chito” in highlight-reel fashion, there’s no telling what’s next for O’Malley. (He should probably just fight Merab Dvalishvili, but you get the picture.)

Vera presents an enormous challenge, and not just because he already owns bragging rights in the rivalry. The consummate company man is being handsomely rewarded for his anytime, anywhere attitude, and he has little to lose and everything to gain. O’Malley is known for his flashy knockouts, but how is that going to work against an opponent that will not stop coming forward for five rounds and has never been finished? Then again, there’s a first time for everything.

Dustin Poirier looks to prove that in the five-round co-main event against Benoit Saint Denis, who is yet to lose in the UFC when competing at 155 pounds. Saint Denis is a juggernaut who has finished his past five opponents and he’s coming to take Poirier’s long-held spot in the rankings. Win or lose, no one can ever say that Poirier isn’t up to face the toughest and hungriest challengers.

In other main card action, Kevin Holland welcomes former Bellator star Michael “Venom” Page to the UFC, one-time welterweight title challenger Gilbert Burns takes on Jack Della Maddalena, and former bantamweight champion Petr Yan aims to stop a career-worst skid when he fights Song Yadong.

What: UFC 299

Where: Kaseya Center in Miami

When: Saturday, March 9. The card begins with a five-fight early prelims portion on ESPN+ at 6 p.m. ET, with continuing coverage of the four-fight prelim card on ESPNews and ESPN+ beginning at 8 p.m. ET. The five-fight main card begins at 10 p.m. ET and is available exclusively on ESPN+ pay-per-view.

Odds: DraftKings Sportsbook


(Numbers in parentheses indicate standing in MMA Fighting’s Global Rankings)

Sean O’Malley (2) vs. Marlon Vera (9)

Bold prediction time: Sean O’Malley by knockout.

As mentioned above, Chito has never been knocked out and that’s no small feat given that he has been in there with some sluggers. He’s incredibly tough and routinely grows stronger as a fight progresses. Add in effective counters, heavy hands, and sharp leg kicks and you can see why he’s a popular pick to upset O’Malley.

It’s the slow starts that have me concerned for Vera. O’Malley isn’t one to just come out guns blazing, but he has a knack for pouncing when his opponents make a mistake or give up too much ground. From their first fight, O’Malley learned the dangers of playing Vera’s game, so he’s likely to change tact here and test Vera’s defense early. This should be O’Malley on the offensive from the opening bell.

That approach comes with risk as Vera will probably be thrilled to see O’Malley marching right into range. But O’Malley’s tricky movement should keep him from absorbing too many damaging blows until he can find the openings he needs to do some damage. That said, nothing in this fight will come easy for either fighter and if it goes into the championship rounds, we’ll have to see a side of O’Malley that he hasn’t had to show before if he wants to retain.

I’m not expecting it to go that far. O’Malley stings Vera somewhere in the first 10 minutes, sending Vera into a spiral that he won’t recover from. From there, O’Malley pours it on for a finish that will silence plenty of doubters.

Pick: O’Malley

Dustin Poirier (T5) vs. Benoit Saint Denis (13)

Benoit Saint Denis has done a brilliant job of bullying his past few opponents and trucking his way to victory. You don’t bully Dustin Poirier.

I can definitely see this one getting hairy for Poirier at the start, especially if Saint Denis is determined to make a statement. Even in the loaded lightweight division, Saint Denis’ physicality stands out and he’s going to win a lot of fights through sheer brute force. That’s not to take away from his all-around skills, which are considerable, but it’s his dogged pursuit of the finish that makes him even more dangerous.

This is where Poirier’s experience comes into play. You could easily make the argument that Poirier’s history of grueling wars makes him ripe for the picking in this matchup, but I’m choosing to focus on the positive. Outside of a handful of elite names, few fighters can dust off “The Diamond” early. He should be able to survive Saint Denis’ opening onslaught and take it to the later rounds where he has the advantage.

Saint Denis is ridiculously durable, so I don’t expect him to go away even as Poirier picks up momentum. However, I do expect Poirier to pull away on the scorecards with a focused striking attack that Saint Denis can’t match at this stage of his development. There are career-defining wins ahead for Saint Denis, he just won’t be adding Poirier to that list this weekend.

Pick: Poirier

Michael Page vs. Kevin Holland (15)

Kevin Holland: Dangerous, unpredictable, and exactly the type of guy to rain on someone’s parade.

The arrival of Michael Page in the eight-sided cage is long overdue and as much as I enjoyed his time with Bellator, he deserves a fresh set of opponents and the UFC presents a number of intriguing challenges at 170 pounds. You couldn’t ask for a better greeter than Holland, who has popularity, a crowd-pleasing style, and sits just on the edge of the top 15. Beating Holland gives Page instant credibility for those unfamiliar with him.

That will be doubly true if he KOs Holland and creates yet another meme-able moment. Page’s showmanship is second to none and his highlights typically generate the kind of mainstream buzz that the UFC and ESPN are desperate for. His slick karate style will give Holland some bad Stephen Thompson flashbacks, but Page is capable of more explosive maneuvers than “Wonderboy” even if he isn’t as consistent as the two-time welterweight title challenger.

Holland won’t be psyched out by any of Page’s theatrics; if anything, sharing the cage with the animated Page will probably embolden Holland to show off his boisterous personality even more. This one could get silly in a hurry.

In the end though, the audience will get the instant classic finish they’re looking for, just maybe not from the fighter they’re expecting. Holland shrugs off a frustrating first round to catch Page in the second and leave him flat on the canvas.

Pick: Holland

Gilbert Burns (5) vs. Jack Della Maddalena (13)

We can glean a lot of data from Jack Della Maddalena’s past two split decision wins, even if they came against opponents with little in common.

Two fights ago, Bassil Hafez put Della Maddalena’s grappling defense to the test. The Australian slugger didn’t do too poorly on the ground, allowing Hafez to maintain control while nullifying much of the UFC debutant’s offense, and did more than enough in the standup to win on the scorecards.

More recently, Della Maddalena had to navigate Kevin Holland’s considerable reach advantage and the results were mixed. His impactful punches earned him the nod, but he almost allowed Holland to drown him with volume. He needs to do a better job of filling in the gaps when he’s not the one pushing forward.

Gilbert Burns presents a physical challenge closer to Hafez than Holland. The top 5 contender is a proven finisher on the feet and on the ground, so I’m curious to see if he focuses on the latter given the success Hafez had with takedowns. If Burns plays it smart and focuses on getting this fight to the ground, it could be a long 15 minutes for Della Maddalena.

Burns mixes the martial arts and takes a decision win.

Pick: Burns

Petr Yan (6) vs. Song Yadong (12)

When you think about it, Petr Yan’s recent struggles aren’t that bad, right?

The first Aljamain Sterling fight, we all know what happened. In a championship fight that Yan would have been leading on the scorecards had it gone to the final round, he launched the most poorly timed illegal strike in history and cost himself a belt. Weirdness.

He bounces back with a fantastic win over Cory Sandhagen, then drops the rematch to Sterling in a razor-close fight. Then he loses to Sean O’Malley in an absolute barnburner that also could have gone his way and then there was a clear-cut decision loss to Merab Dvalishvili.

Outside of that last setback, there’s plenty of reason to believe that Yan is still that dude at 135 pounds, so I’m picking him. That’s right, I’m going with all the higher ranked fighters this Saturday. UFC 299: Hold Serve.

At some point, I should probably stop doubting Song Yadong (I did correctly back him in his most recent fight against Chris Gutierrez). He’s improved every year he’s been in this business while not getting away from the fan-friendly style that brought him to the dance. But can he win a standup battle against Yan, who I still consider to be one of the best boxers in MMA?

The younger Song likely takes Round 1, but Yan’s greatest strength is his ability to analyze and adjust. He’ll take five minutes to download Song, then unleash hell in the next 10. Nothing would make me happier than Song proving me wrong. For now, I have Yan putting on a vintage striking performance and breaking out of his slump.

Pick: Yan

Preliminaries

Jailton Almeida def. Curtis Blaydes

Maycee Barber def. Katlyn Cerminara

Mateusz Gamrot def. Rafael dos Anjos

Pedro Munhoz def. Kyler Phillips

Philipe Lins def. Ion Cutelaba

Michel Pereira def. Michal Oleksiejczuk

Robelis Despaigne def. Josh Parisian

Assu Almabayev def. CJ Vergara

Joanne Wood def. Maryna Moroz