UFC 299: O’Malley vs. Vera 2 Preview and Predictions

On Saturday night, Miami, a city known for its extravagance. plays host to one of the most flamboyant UFC champions, as Sean O’Malley puts his bantamweight championship on the line against Marlon “Chito” Vera in a rematch of O’Malley’s only professional loss. When the pair of elite bantamweights met the first time, a kick from Vera damaged the peroneal nerve in O’Malley’s leg and Vera was able to capitalize and score a first round TKO by punching O’Malley’s head nearly through the canvas. Since that fight, O’Malley has still claimed to be an undefeated fighter as he marched towards the title that he won by defeating Aljamain Sterling. Vera is out to prove that the first meeting was no fluke and rip the title away from O’Malley.

The co-main event takes place in the star studded lightweight division, as former interim champion Dustin Poirier gives a huge opportunity to Benoit Saint-Denis, the twelfth-ranked fighter. Poirier is coming into this fight on the heels of a loss, suffering a knockout loss to Justin Gaethje with the BMF title on the line. Saint-Denis has been streaking, rattling off five straight wins by finish since dropping his UFC debut. A win over a legendary fighter like Poirier would be a huge feather in Saint-Denis’s cap as he looks to make a push for title contention.

Also on the main card, former Bellator standout and Karate champion Michael “Venom” Page makes his UFC debut as he clashes with the always entertaining Kevin Holland. Holland is a crowd pleaser who willingly put himself in a kickboxing match against Stephen “Wonderboy” Thompson and fans are in for a treat if he decides to do the same thing against Page this weekend. Former welterweight title challenger Gilbert Burns returns to action, after sustaining an injury in his last fight against Belal Muhammad, and he is pitted against rising contender Jack Della Maddalena. Opening up the main card is a bantamweight showdown with former divisional kingpin Petr Yan looking to snap a three fight losing streak and slow down the hard charging Yadong Song.

The UFC 299 early prelims air live on ESPN+ and UFC Fight Pass starting at 6 p.m. ET, followed by the preliminary card on ESPN+, ESPNEWS and ESPN at 8 p.m. ET. The main card airs on ESPN+ pay-per-view at 10 p.m. ET. Combat Press writers Dan Kuhl and Matt Petela preview the action in this week’s edition of Toe-to-Toe.

The first time Sean O’Malley fought Marlon “Chito” Vera the bout ended with some controversy and a Vera victory; does O’Malley avenge his only career loss in the rematch?

Kuhl: There was a time when I thought Marlon “Chito” Vera was the next big thing. A lot of people did. He entered The Ultimate Fighter: Latin America with a record of 8-1-1, and seven of his wins were by stoppage. He scored a knockout on TUF to get his UFC contract, and that was nearly a decade ago. By the time he faced Sean O’Malley the first time, he was 17-6-1 with all of his losses by decision and almost all of his wins by finish.

At UFC 252 in Aug. 2020, O’Malley came out throwing effective leg kicks, but ended up with an injured leg himself, which set up Vera to get the TKO victory. Since then, Vera lost to former featherweight king Jose Aldo, and two fights ago, he dropped a split decision against Cory Sandhagen where he looked completely flat, and that should have been a unanimous decision loss. Between Aldo and Sandhagen, Vera went on a four-fight winning streak, which included knockouts of two other former champions in Frankie Edgar and Dominick Cruz, and his last outing was a decision victory over Pedro Munhoz.

After his loss to Vera, O’Malley scored three knockouts in a row, before an accidental eye poke rendered Munhoz unable to continue when the two faced off in Jul. 2022. Then he picked up a split decision over Petr Yan, followed by his title-winning performance over Aljamain Sterling. So, in the rematch, I have to side with the champ O’Malley.

O’Malley has better grappling and an effective counter-striking style. He also can use his range to manage distance against Vera. We know O’Malley will be on point in all aspects of his game, but it’s hard to predict what we will get out of Vera, especially after the Sandhagen performance. Chito Vera does have a chance to score a victory, and he’s a moderate +210 underdog, but I think O’Malley will score a TKO victory before the championship rounds, picking Vera apart along the way.

Petela: The only loss in Marlon Vera’s last five fights is that performance against Cory Sandhagen that Dan mentioned.That was a confusing performance, it seemed like Vera never really got out of second gear. Not to take anything away from Sandhagen, who has a peculiar style, but that wasn’t the best version of “Chito.” In this grudge match, Vera will be on point from the onset, and I don’t think he will allow O’Malley the space to get into his flow state.

O’Malley is a tremendous fighter, no doubt about it, but he is also an entertainer. Sort of like if the star quarterback was also the class clown. He adds flare to all of his fights, whether he is pretending to play basketball or doing the Ali shuffle. He won’t be able to do that against Vera in this matchup. As the shorter fighter, Vera will have to close the distance and get inside of O’Malley’s length. As a longtime student of Jason Parillo, Vera knows exactly how to maintain a distance where he can land punches, but not be too close for O’Malley to fully extend and put that snap on the end of his punches that has proven to be devastating.

Vera will frustrate O’Malley throughout this fight. O’Malley won’t be given the space to showboat after connecting with a big punch because Vera will be right back in his face making him pay. There will certainly be damage on both sides, and Vera isn’t going to leave the fight without a few bumps and bruises, but it will be no worse than when you cut the corner too sharp and bang your shoulder on the edge of the cabinet. Vera outclasses O’Malley and wins a lopsided decision.

The highly anticipated co-main event pits divisional mainstay Dustin Poirier against relative newcomer Benoit Saint-Denis; will this fight be a changing of the guard or will the veteran hold off the next generation for a little while longer?

Petela: This fight just seems different. There are many lovable fights, but this one stands out unlike any other. It is happening at the perfect time, with Benoit Saint-Denis’s profile on the rise, and Dustin Poirier ready to make one last run at gold. The stars aligned, and, despite a little pre-fight confusion on whether or not the deal was signed, this fight could be one for the ages. I don’t think I am being hyperbolic when I say that.

We know that Dustin Poirier is an elite, well-rounded mixed martial artist with superb boxing and a black belt in jiu-jitsu. He has been to the top of the division, once holding interim gold, and, despite a setback in his most recent fight, he still has the talent and experience to defeat anyone on the planet at 155 pounds. Saint-Denis is a fast-rising prospect turned contender who grows by leaps and bounds each time he fights. His only loss in the UFC was his debut, which he took on short notice and up a weight class. He took a hellacious beating in that fight against Elizeu Zaleski dos Santos, but showed a level of toughness that not even other mixed martial artists can rival. He has the makings of a superstar with the backing of an entire country, as the French MMA scene is growing rapidly.

I think we see an instant classic in this one. Poirier will prove that he still has plenty of juice left, and Saint-Denis will show that he is one of the best in the world.This one goes the distance and the Frenchman picks up, by far, the biggest win of his career and announces himself as a threat to the crown. Poirier’s stock doesn’t drop though, as he will still have a few more elite performances before it is all said and done.

Kuhl: I almost completely agree with everything Matt said, including the outcome of the fight. Dustin Poirier has a lot of miles on his chassis, and even though he is still only 35 years old, the type of head-kick knockout that he took from Justin Gaethje last summer can take years off your career. Benoit Saint-Denis is the younger, fresher fighter, who is on the come-up, and he will likely outwork Poirier over three rounds, even if by a razor-thin margin. Where I disagree with my colleague is in the aftermath.

Poirier has only lost two of three fights once in his career before now, and he has never lost three of four. He has a family, a hot sauce, and a bourbon, and he has more than made his bag in MMA. He no longer needs to work, and he certainly does not need more head trauma. If he loses this one, I see him hanging it up for good. There is just no reason for him to keep fighting, unless he pulls off the win and gets on track for another title shot.

Who’s the biggest winner at UFC 299?

Kuhl: Sean O’Malley. He will get back his only loss in his first title defense, and you can’t get much better than that. While Merab Dvalishvili is the natural next contender to the throne, if, somehow, Cory Sandhagen was to get that shot first, that would be the more interesting match-up for O’Malley from a stylistic perspective.

Petela: Benoit Saint-Denis. Dustin Poirier is doing him a major favor by giving him this opportunity and the former French special forces operator will capitalize in a big way. By beating Poirier it will open up big names and highly ranked fighters for Saint-Denis, though it wouldn’t surprise me if more than a few people start avoiding him after seeing how he rises to the occasion in the biggest moments.

Who’s the biggest loser at UFC 299?

Petela: It has to be Petr Yan. He has lost three fights in a row and is opening up the main card on the same night that the belt he once held is at stake in the main event. A fourth straight loss will be devastating and it will put the former champion well outside the possibility of ever contending for the title again. He certainly has the ability to defeat Yadong Song but I don’t expect him to come out with a win. He probably won’t be cut by the UFC but his place among the division’s elite will be long gone.

Kuhl: Curtis Blaydes. This sounds weird to say, because he has fared really well in one of the shallowest divisions in MMA, but as good as he has been, he has never gotten a sniff of a title shot. He is a wrestling-heavy fighter with all four career losses coming by knockout, and Jailton Almeida is a bad match-up for him. Blaydes is a good wrestler, but Almeida is a BJJ black belt with far superior grappling skills. On the feet, Almeida could also pick him apart, and he displayed dominance over Derrick Lewis in his last outing, which was supposed to be against Blaydes before Blaydes pulled out. Almeida wins this one handily, forever relegating Blaydes to gatekeeper status for as long as he keeps fighting.

What one fighter’s UFC career is on the ropes at this event?

Kuhl: I don’t see how the loser of the Joanne Wood-Maryna Moroz fight keeps her job. Both ladies have not fared well in recent years. Wood is 1-3 in her last four fights, with one win and one loss by split decision, and her other two losses coming by submission. The kickboxer has only been stopped by submission, but three of the five have happened in the last three and a half years. Moroz took a hiatus in 2021, and since then, she has gone 1-2, and she enters the Octagon with back-to-back losses. Another loss for either of these two could earn the proverbial pink slip.

Petela: Josh Parisian. With all due respect to the man, the UFC is kind of running out of new heavyweights to break into the organization by beating up Parisian. He has lost four of his six bouts inside the promotion, including two in a row. A loss to a debutant like Robelis Despaigne will be the end of the road for him with the organization and he will likely find himself fighting out the remainder of his career on the regional or international scene.

Which fight is the sleeper match-up on this card?

Petela: The lightweight preliminary matchup between Mateusz Gamrot and Rafael dos Anjos. Gamrot’s only setback in the UFC came against Beneil Dariush and he has won two straight since that outing. He is improving each time he steps into the cage and will be the best version of himself this weekend. Dos Anjos is slightly past his prime and has bounced back and forth between lightweight and welterweight. He is still very talented and may still pose a threat. If Gamrot is able to get by RDA, it is a good sign that he is ready to compete with the most elite fighters in the world. Also, if dos Anjos comes up short it is likely a sign that he is now moving firmly into the gatekeeper role and his future might be a bit opaque inside the promotion.

Kuhl: I’m loving Michel Pereira vs. Michał Oleksiejczuk. We just haven’t seen enough Pereira in recent years, mostly due to opponents pulling out. However, he won his last outing in OCt. 2023 when he crushed Andre Petroski in only 66 seconds. Oleksiejczuk, on the other hand, has been around the UFC fairly consistently for the last six years. He has won some and lost some, and he always puts on an entertaining fight. In his last bout, he also scored a first-round finish, which was a TKO of Chidi Njokuani. Both of these guys are coming in ready to bang, and this one might not make it out of the first round.

Who takes home the “Performance of the Night” honors?

Kuhl: Michael “Venom” Page. It’s pretty rare that we see a Bellator standout cross over to the UFC, but MVP is coming in with a huge fight against Kevin Holland. Holland is a striker, first and foremost, but he does have great grappling. With MVP’s dynamic striking, Holland is a showman that will likely be ready to put on a display, but that will get him caught by MVP, who will earn some extra cash.

Petela: Gilbert Burns. It is time for Burns to make one last push towards the title and he will begin to do just that by thwarting the hype train of Jack Della Maddalena. Burns will have to avoid the firepower of Della Maddalena but once this fight gets to the canvas, it is a wrap. Burns will lock in his tenth professional submission victory and pull in more cash than someone running an empire selling used items on Facebook Marketplace.

Pair this card with…

Petela: A blueberry crush. First of all, they are delicious. Second of all, they are the unheralded one in the group of “crush” drinks. Most people go with the higher profile orange crush, which is fine, but it has too much hype around it just like the upcoming UFC 300. Blueberry crushes, like UFC 299 are stuck playing second fiddle despite being superior. Just make sure that you don’t end up with blueberry bits stuck in your teeth.

Kuhl: I was first introduced to the Goombay Smash in Miami back in 1999. It is a Bahamian tropical cocktail, consisting of coconut rum, apricot brandy, pineapple juice and passionfruit juice with a dark rum floater. It is served over ice in a tall glass, and is both strong and refreshing. This card is going to involve plenty of strong and plenty of smash, but it will also be refreshing as we get to see a lot of the newer faces of the UFC, including Jailton Almeida, Benoit Saint-Denis, Jack Della Maddalena, and, of course, Michael “Venom” Page. The Goombay Smash will be the perfect pairing for this Miami event.