UFC 299 Predictions: Sean O’Malley vs. 'Chito' Vera, Dustin Poirier vs. Benoit Saint-Denis

Before the action starts, take a look at our UFC 299 picks.

Fight night is almost here, and we've got our UFC 299 main card predictions.

While UFC 300 will be taking place next month, there is a stacked pay-per-view card going down this Saturday night. UFC 299 will be headlined by a UFC Bantamweight Championship clash between titleholder Sean O'Malley and Marlon "Chito" Vera. Many are expecting the co-main event to be a banger as Dustin Poirier will meet Benoit Saint-Denis.

Fight fans have been anticipating the UFC debut of former Bellator star Michael "Venom" Page and the wait is finally over. He will go one-on-one with Kevin Holland. UFC welterweight contender Gilbert Burns is set to collide with the rising Jack Della Maddalena, and former bantamweight champion Petr Yan opens the main card against Song Yadong.

Without further ado, let's get on with the UFC 299 predictions.

Sean O'Malley (c) vs. Marlon "Chito" Vera - for the UFC Bantamweight Championship

(via Zuffa LLC)

Fernando Quiles Jr: "Chito" Vera is one tough customer. He can take a lot of punishment and still move forward. I think there will be some close calls for O’Malley in this one. I can see Vera getting tagged with some clean punches, yet still be standing by the end of the horn. I think O’Malley takes a tough decision win. (Pick: O’Malley)

Drew Beaupré: The biggest factor for me in this matchup is that the Sterling fight was the only time O’Malley has even been scheduled for five rounds, while we’ve seen “Chito” go 25 minutes on more than one occasion. Vera’s output in the early rounds could hamper his chances of winning a decision, but it’s hard to picture O’Malley knocking him out considering how insanely durable the Ecuadorian has been throughout his career. (Pick: Vera)

Zain Bando: I have had the luxury of following Sean O’Malley’s UFC career from his DWCS victory in Aug. 2017. His brash persona, “undefeated” mantra and flashy fighting style is what drew me in back then and still does today. Since his loss to Marlon Vera in Aug. 2020, he has since gone unbeaten with no signs of slowing down. He is already talking about big fights down the road – newly minted featherweight champion, Ilia Topuria, as an example – and who can blame him? He has all the momentum in the world at the moment, and although Vera might have the tools to beat him, the championship experience is too much to overlook. O’Malley gets it done by a third-round KO or a close decision. (Pick: O’Malley)

Consensus: 2-1, Sean O’Malley

Dustin Poirier vs. Benoit Saint-Denis

(via Zuffa LLC)

Fernando Quiles Jr: There's a lot of hype surrounding Benoit Saint-Denis, but I think "The Diamond" derails that train. Saint-Denis is tough and aggressive, but he hasn't faced nearly the level of competition you would expect from an opponent of Poirier. Dustin knows what it's like to fight elite 155-pounders, something Saint-Denis will experience for the first time. I'll take Poirier here via TKO. (Pick: Poirier) 

Drew Beaupré: It’s wild to see Poirier as an underdog against a fighter that’s only just broken into the lightweight rankings, but Saint-Denis has been impressive since that short-notice debut at welterweight against Elizeu Zaleski. The Frenchman showed off how devastating his kicks can be against Frevola, but even after seeing Poirier get head kicked in the Justin Gaethje rematch I have to take “The Diamond” to beat the odds and remind fans he’s still one of the best fighters in the world. (Pick: Poirier)

Zain Bando: Having spoken to Dustin Poirier a little over a week ago, I can confidently say his head is in the right place. He recognizes what a dangerous and young opponent Benoit Saint-Denis is and how he cannot overlook him by any stretch. 

There are two factors at play when picking the former UFC interim lightweight champion and two-time lineal lightweight title challenger. First, championship experience. Poirier has been fighting for titles in some capacity every few years since April 2019. The Saint-Denis fight is a rare non-title five-rounder, more common in today’s UFC than in years past. BSD has yet to experience the championship rounds, and, to me, the longer the fight goes, the better off it favors ‘The Diamond.’ Arguably the most critical aspect is longevity.

Poirier has been with the promotion since Jan. 2011, whereas BSD joined the big leagues less than five years ago. Not to mention the fact that Poirier hasn’t been outside of the top-15 rankings, regardless of division, in a decade. 

That’s next-to-impossible to compete with, let alone comprehend holistically. Nonetheless, Poirier is the better fighter, and with dozens and dozens of family members and friends traveling by way of New Orleans to Miami, the unofficial hometown crowd should have a local favorite on fight night. Poirier gets it done with a TKO victory, proving he is still one of the best lightweights in the world. (Pick: Poirier)

Consensus: 3-0, Dustin Poirier

Kevin Holland vs. Michael "Venom" Page

(via UFC broadcast)

Fernando Quiles Jr: Holland's MMA game has vastly improved over the years. He's quite well-rounded, but he has a habit of falling in love with the striking. He could be lured into a trap doing that against someone with the superb standup of "Venom." I think Holland plays with fire early on before eventually getting Page to the ground and submitting him. (Pick: Holland).

Drew Beaupré: This might be the hardest fight to predict on the card, simply because of how hard it is to guess what Holland’s game plan will be. He’s clearly the more well-rounded fighter, but the matchup with “Wonderboy” showed that he’s more than happy to forgo strategy in order to test his striking skills and try to put on an entertaining fight for the fans. I expect this to be a weird one no matter how it plays out, and I’ll side with Holland to spoil Page’s UFC debut. (Pick: Holland)

Zain Bando: UFC jitters are UFC jitters. There is no other way to put it. If Kevin Holland can outwrestle Michael Page and avoid big shots, he should have little trouble getting the job done and spoiling Page’s debut. (Pick: Holland)

Consensus: 3-0, Kevin Holland

Gilbert Burns vs. Jack Della Maddalena

(via Zuffa LLC)

Fernando Quiles Jr: This should be a fun one. I'm just hoping we get the same version of "Durinho" that showed up against Khamzat Chimaev. Maddalena has solid boxing, and if he can stay consistent with the jab it could give Burns problems. I think Maddalena's takedown defense will also play dividends throughout the fight. Give me a decision for Jack Della. (Pick: Maddalena)

Drew Beaupré: Like the Poirier vs. Saint-Denis matchup, I’m a bit surprised to see Burns as an underdog here. Della Maddalena is a well-rounded fighter with all kinds of hype around him, but his biggest win so far was that uninspiring split decision against Holland. Even if Burns is getting to the end of his career, I’ll pick the veteran to at least temporarily halt Della Maddalena’s rise through the welterweight rankings. (Pick: Burns)

Zain Bando: I expect an all-out war between these too, but Burns is just a little crisper and will likely have a bigger in-person fanbase. JDM is a future title challenger but needs more victories against top contenders before entering a further discussion regarding taking over welterweight. Burns should win a decision here or secure a late stoppage. (Pick: Burns)

Consensus: 2-1, Gilbert Burns

Petr Yan vs. Song Yadong

(via Zuffa LLC)

Fernando Quiles Jr: Make no mistake about it, Petr Yan is still dangerous. His losses have come against elite competition, but he's mixing it up with a surging contender. While I think Yan will need to start this fight off aggressively, I feel the speed of Yadong will be too much and he'll fall behind on points as a result. It wouldn't surprise me if Yadong is able to cut off the Octagon, not allowing Yan to take the center of the cage. (Pick: Yadong)

Drew Beaupré: I’m glad that Yan took a bit of time off following his recent run of tough results, but the former champion is desperately in need of a win here if he wants to get back into the bantamweight title picture. “No Mercy” will need to start with an uncharacteristic amount of urgency in order to avoid falling behind in the early going, and while I expect Song to provide a stiff test I’ll side with Yan to take a decision in what should be an entertaining scrap. (Pick: Yan)

Zain Bando: Until Petr Yan shows me something spectacular that replicates the once-peak championship form he once had, I might reconsider this fight. However, with how Thursday’s presser went, Yadong’s demeanor was serious but confident, leading me to believe Saturday night will be another chapter in his entertaining career. Yadong will win by decision, as I believe Yan’s chin can still hold up against anyone at 135 pounds. (Pick: Yadong)

Consensus: 2-1, Yadong

MMA Knockout Staff 2024 Records

• Fernando Quiles Jr: 7-3
• Mathew Riddle: 4-6
• Drew Beaupré: 7-3
• Zain Bando: 4-6
• Christopher De Santiago: 4-1

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