UFC 299: Main Card Predictions

Where has the time gone? Just like that, we are now on to the third UFC PPV of 2024. The promotion is clearly not coasting towards the big UFC 300 event. Every card in the lead-up to the company’s 300th pay-per-view has been nothing short of spectacular.

UFC 299 features a stacked card going down in Miami, Florida. It will be headlined by one of UFC’s next cash cows in Sean O’Malley. He looks to right his wrong by taking on Chito Vera in their highly anticipated rematch for undisputed bantamweight gold. In the co-main, we’ll see one of many matches that feel like a changing of the guard. Dustin Poirier takes on the surging Benoit Saint-Denis in a potential FOTY candidate.

Check out our Staff Predictions:

Bantamweight Championship Bout

(C) Sean O’Malley vs. (5) Marlon Vera

Anik: Styles make fights, and that is why we are getting Sean O’Malley vs. Marlon Vera. While Vera arguably has the best chin in the bantamweight division, O’Malley can use his long range to jab him apart like Rob Font did in the early rounds of their fight. Vera needs to get going early, or else he will be down on the scorecards. I believe his only path to victory is catching O’Malley with a thunderous shot. We will be hearing Bruce Buffer yell “and still” by the end of the night, and O’Malley will get his revenge.

Official Prediction: Sean O’Malley via Unanimous Decision 

Mishal: Strangely enough, both men in the main event are stylistically one another’s toughest fight. O’Malley is a master of finding anybody’s chin, while Vera has the best defense in the bantamweight division. The challenger has never been dropped or cut in his career, and the champion has a history of being able to do both. Vera can make this a scrap as long as he doesn’t take too long to get into the fight. But, something just tells me this won’t happen. His best bet is to make this dirty, and fast, against a champion we know will be looking for the smallest of openings.

Vera is a notoriously slower starter. But in his last-round fight against Cory Sandhagen, he was unable to get anything meaningful going… O’Malley is a puzzle for virtually any fighter. While their limited time in the octagon was closer than most would admit, I find it hard to believe that the challenger has the tools necessary to break the champion.

Official Prediction: Sean O’Malley via Unanimous Decision

Evan: As much as I feel this rematch is a bit of a disservice to the rest of the division, I’m still excited to watch these two run it back again. O’Malley has matured as a fighter since that first defeat to Vera. However, I feel much of the stylistic problems Chito presented Sean in their first outing at UFC 252 remain the same now. Marlon’s combination of incredible durability, ruggedness, and overall versatility are an interesting contrast to the elusiveness, craftiness, and impeccable timing Sean brings to the table. 

Chito tends to get better as the fight goes on. So the longer this fight lasts, the more I favor Vera’s skillset. I think he limits O’Malley’s movement with the kicks as he did in their first meeting. He’ll push Sean to the cage to utilize the clinch, where he can punish him with dirty boxing, knees or elbows. Chito could also work in some occasional takedown attempts to force Suga to grapple at times.

Official Prediction: Marlon Vera via Unanimous Decision

Lee: Marlon Vera dominated the first fight by using leg kicks and effective striking at a distance.  I expect the same type of game plan from Vera. But, I think he mixes in some wrestling which is easily O’Malley’s biggest weakness. Can O’Malley use his slick striking and constant movement to stifle Vera?

Official Prediction: Sean O’Malley via Split Decision

Marcos: This is far more than just a title defense for UFC bantamweight champion Sean O’Malley. Because of that, I think we see a very intriguing main event. Chito Vera is responsible for the only loss in O’Malley’s career, and that certainly gives him the confidence to go out and do it again. This time, for undisputed gold. Although Vera has a very effective stand-up game, it pales in comparison to the dynamic kickboxing ability of the champion. Perhaps Vera’s best route would be to finish it on the ground like he did the first time. But without O’Malley’s foot being compromised in this one, that will be far more difficult.

Official Prediction: Sean O’Malley via Unanimous Decision

(3) Dustin Poirier vs. (11) Benoit Saint-Denis

Anik: Out of all the barnburners created between UFC 297 to UFC 300, this might be the best one. Saint-Denis served in the French military in a role similar to Navy SEALs, and people don’t realize how tough he is. In a fight where I expect both to take damage, Saint-Denis has the fresher chin to handle it all. I expect an absolute barnburner, where neither fighter gets tired. I’m picking the slicker fighter to be smart amidst a bunch of striking exchanges. I think the Frenchman can pull off a submission.

Official Prediction: Benoit Saint-Denis via 4th-Round Submission

Mishal: My main event. A collision between one of my favorite all-time fighters, and a newcomer with fire behind his eyes. If you’re placing your bets on the FOTN, this is likely on a card filled with banger after banger. This is as dangerous as it gets. Saint-Denis is one of those who loves violence. But his veteran opponent is at his best when things go there. Poirier’s defense, pocket boxing and guard are difficult to penetrate. Something does tell me though that Saint-Denis’ will find his way through over 25 minutes. I don’t see this fight going the distance.

Official Prediction: Benoit Saint-Denis via 4th-Round KO/TKO

Evan: One of the things that worries me with a lot of these fights, is they truly are “changing of the guard” type matchups. If you haven’t noticed by now, we feed the old to the young in this sport. Fighters that compete in these weight classes tend to start fading fast from the age of 35 onward. All of those factors, paired with Dustin Poirier coming off a brutal head kick KO loss in his rematch to Justin Gaethje are a recipe for disaster against a punisher like Benoit Saint-Denis.

I could see the Frenchman beating one of Louisiana’s favorite sons to a bloody pulp in this one. However, Saint-Denis gets hit a lot in his fights—according to UFC Stats, he absorbs a lofty 5.2 significant strikes per minute. I think that willingness to take damage might come back to haunt him against a puncher with the finishing instincts Poirier possesses. I’m hesitantly going to pick Dustin in this fight. Expect a FOTY contender from these two, don’t blink when you watch this one.

Official Prediction: Dustin Poirier via 4th-Round KO/TKO

Lee:  I have to admit, I did not like the way Poirier looked against Justin Gaethje. Gaethje pressed the action against Poirier to secure a second-round KO/TKO victory. Saint Denis’ thirteen wins have all ended by finish. Poirier is the more experienced and well-rounded fighter, but can he regain his championship form? I think so…

Official Prediction: Dustin Poirier wins via Unanimous Decision

Marcos: In this fight, we see a longtime veteran take on a new contender in what is arguably the strongest weight class in all of the sport. This is a fight that will determine whether Dustin Poirier can still hang at the top of 155 pounds and has the potential to bring forth a new threat to Makhachev’s reign. Especially coming off a knockout, this is a very dangerous fight for Poirier to be taking. Saint-Denis is 4-0 at lightweight so far, and he is the younger fighter. If this turns into a stand-and-bang affair, I favor the boxing of Poirier enough to get it done. However, with Saint Denis’s strong offensive grappling and kicks, he should have the tools to get the win. Expect a new threat in the lightweight division after UFC 299. 

Official Prediction: Benoit Saint Denis via 3rd-Round Submission

(13) Kevin Holland vs. Michael Venom Page

Anik: In a matchup of two true exciting strikers, let’s see what will win rounds. MVP has extravagant moves, but must be careful of getting caught by the Holland strikes. Both are extremely fast, but if Holland needs to steal rounds, he can easily land takedowns. As the fight goes on, MVP will become more desperate for the knockout blow. In that pursuit, I believe Holland catches him and sends the former Bellator star to the canvas.

Official Prediction: Kevin Holland via 3rd-Round KO/TKO

Mishal: The overdue wait for MVP’s arrival in the UFC is finally over. But Kevin Holland is as crafty as they come. He takes on anyone and everyone, and has a solid ground game pair with decent stand-up. It will all be put to the test against the unpredictability MVP brings into each fight. His calibre of opponents in Bellator isn’t what he’ll be used to seeing in the UFC. As excited as it is to have him on the roster, my gut feeling is his arrival is a little too late. This should be a fun one, but I lean with the inconsistent Kevin Holland.

Official Prediction: Kevin Holland via Unanimous Decision

Evan: I could see this fight playing out eerily similar to Kevin Holland vs. Stephen Thompson back in December 2022. Page has a style and tools that are very reminiscent of Thompson’s… So it wouldn’t surprise me at all if MVP outclasses Kevin with superior counterpunching skills in what amounts to a kickboxing match. Nevertheless, I think Holland turns this into as chaotic of a scrap as he possibly can. His length, underrated power, and tricky submissions are going to cause issues for Michael’s ability to find his striking rhythm. I feel he’ll be able to catch Page with a big shot on the feet and create a grappling scramble. It will end up leading to a finish of some sort.

Official Prediction: Kevin Holland via 2nd-Round TKO or Submission

Lee: MVP makes his UFC debut against a very game Kevin Holland. This fight should have some exciting striking exchanges and trash-talking galore. The fighter who can win the last thirty seconds of each round will win this fight. Holland has the reach advantage and has fought more top-tier opponents.

Official Prediction: Michael Page via Split Decision

Marcos: Given the styles of both fighters, this matchup can steal the show at UFC 299. One of the hottest free agents in all of MMA has signed to the UFC. He now looks to leap right into the rankings with a win over a tough Kevin Holland. Oftentimes, it seems as though Holland chooses the hardest route to victory in a fight. It would not shock me if he attempted to engage in a straight kickboxing match with MVP. But, even if Holland chooses to execute his game plan, I still see him struggling to work his wrestling in this fight. My only potential concern with Michael “Venom” Page is the fact that he is 36 now and entering the UFC. But for this fight specifically, I do not see that as an issue.

Official Prediction: Michael Page via Unanimous Decision

(4) Gilbert Burns vs. (11) Jack Della Maddalena

Anik: This fight is a true test to see whether there’s a changing of the guard in the welterweight division. While Jack Della Maddalena has won his last two fights by split decisions, they were both on short notice. Whenever he fights with a full camp, he has looked as crisp as ever. This is purely a striker vs. grappler matchup. But it concerns me that Burns’ recently made comments that Belal Muhammad does not deserve a title shot. Father time is undefeated, and I’m picking JDM to win two rounds by keeping it on the feet.

Official Prediction: Jack Della Maddalena via Unanimous Decision

Mishal: JDM has some of the smoothest boxing combinations in the UFC. He goes up against a grappler in Gilbert Burns who isn’t afraid of a firefight. Burns has some serious power in his hands, hurting the very best in the welterweight division since 2019. But, he may need another game plan this time around. Burns will need to utilize his grappling prowess to bring him his openings rather than trade on the feet with the far superior striker. This is no easy fight for the former title challenger to come back from an injury to face. His Australian opponent has been on an absolute tear… A 16-fight win streak with his last loss coming in 2016.

Official Prediction: Jack Della Maddalena via Split Decision

Evan: This fight is another potential embodiment of matchups where you could see an older star being led out to slaughter for an emerging young contender. It very much worries me as a Burns fan that he’s now 37-years-old. He’s competing at welterweight and is also coming off a torn AC joint injury that he suffered in his most recent appearance against Belal Muhammad. I’m confident that his grappling abilities are far greater than JDM’s though. So, it wouldn’t shock me to see him run over the Australian contender on the mat. I’m putting my confidence behind JDM’s stellar 82% takedown defense rate to thwart off Burns attempts to get this fight to the ground.

Official Prediction: Jack Della Maddalena via Unanimous Decision

Lee: This fight has the makings to be the most evenly matched fight of the evening. Both fighters possess elite striking skills. But, Burns holds the upper hand if the fight goes to the mat. The fighter that implores his game plan and will first will win this fight.

Official Prediction: Gilbert Burns via 3rd-Round Submission

Marcos: This will be the toughest test in the career of Jack Della Maddalena. Gilbert Burns is certainly the more experienced fighter, but he’s getting older. JDM is now in the prime of his career at 27 years old. However, he has never faced someone the caliber of “Durinho”. Burns will need to land some takedowns to win this fight… But with the solid takedown defense of Maddalena, that will be difficult. It appears that JDM has the speed advantage in the striking, and I think that will make a difference. I expect Maddalena to win a very close decision in this one. But it could go either way…

Official Prediction: Jack Della Maddalena via Split Decision

(5) Petr Yan vs. (7) Song Yadong

Anik: This fight arguably has the highest stakes over everyone not in the main event. The winner can catapult themselves into a number one contender fight next. Yan has always been a slow starter, and he could be down a round before he even realizes it. Yadong proved his newfound patience in his last two fights, and he hits like a truck according to past opponents. I’m going to choose power over volume this time, and I believe we could be bringing the UFC back to China.

Official Prediction: Song Yadong via Unanimous Decision

Mishal: You know a card is stacked when this is your opener. Yet another fight that is almost too close to call. Petr Yan is 1-4 in his last 5, only losing out to elite competition in this period. Yadong, however, is 4-1 in his last 5 and has only been growing with each performance. Both men are supremely well-rounded strikers with finishing capability. The one key factor here is the three-round setting of this fight… Yan’s style is better suited for a 25-minute affair, something that Yadong has shown he is more capable of adapting his style to effectively. I do see this being highly competitive and largely on the feet since both men possess excellent takedown defense. But, I’m riding with the underdog.

Official Prediction: Song Yadong via Split Decision

Evan: This fight is a true coin flip for me. While Yan might currently be on a three-fight losing skid, I’m not sure it’s necessarily an indicator of some crazy regression he’s suffered as a fighter. He lost close split-decisions to the last two champions of the division in Aljamain Sterling and Sean O’Malley. He then was defeated by a guy in Merab Dvalishvili who’s running through everyone at the moment… So it shouldn’t diminish Yan’s standing in fans or pundits eyes. He’s still one of the most skilled fighters in the entire sport. I’m going to put my money on the Russian to get things going in the right direction here.

Official Prediction: Petr Yan via Unanimous Decision

Lee: Yan likes to use his striking ability to gain an advantage while putting his opponent on their back foot. But Song is an effective striker with precise offense. The height, weight, and reach comparison is about even in what I expect to be one of the best fights of the night.

Official Prediction: Song Yadong via Split Decision

Marcos: In this one, we see perhaps the most technical bantamweight on the roster take on one with legit knockout power. Song Yadong has shown some legitimate improvements over the last few years, and Petr Yan has lost three very close fights to some of the best guys on the planet. I would give a slight edge in boxing to Yan and a slight edge in grappling to Yadong, making this a very exciting matchup. Given the top-level competition that Petr Yan is used to and the fact that he feels he was robbed a couple of times in his last few fights, I think he will bounce back in a big way. I still expect to see a war with two very capable bantamweights.

Official Prediction: Petr Yan via Unanimous Decision

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