Fight By Fight Preview | UFC 299: O'Malley vs Vera 2

New champ Sean O’Malley defends his title for the first time against the only man to have bested him thus far, Marlon “Chito” Vera, in the UFC 299 main event.

O’Malley completed his rise through the bantamweight ranks with a second-round knockout win over Aljamain Sterling last summer in Boston. The OG breakout star from Dana White’s Contender Series (DWCS) landed a clean right hand to close out the contest, advancing his record to 17-1 with one no contest in the process.

Vera dropped his opening assignment of 2023, landing on the wrong side of the cards in a scrap with Cory Sandhagen that was scored as a split decision, but wasn’t that close. He bounced back with a unanimous decision win over Pedro Munhoz the same night O’Malley claimed the title and has won five of his last six.

These two first met at UFC 252 in August 2020, with Vera winning by first-round stoppage after deadening O’Malley’s left leg with a perfectly placed low kick. “Suga” has been salty about the result ever since, and when the opportunity to avenge his loss in his first title defense presented itself, the 29-year-old champion jumped at the chance.

Bad blood, a championship fight, and two of the most consistently entertaining competitors in the deepest division in the sport — what a way to close out the show!

Other Main Card Fights

Dustin Poirier vs. Benoit Saint Denis

Veteran Dustin Poirier and surging French standout Benoit Saint Denis face off in this rare five-round co-main event.

Poirier has been a fixture towards the top of the lightweight division for the last seven years and counting, claiming an interim title and challenging for undisputed gold twice while amassing a 9-3 record with one no contest during that span. Now 35 and coming off a second-round knockout loss to Justin Gaethje, questions about how much “The Diamond” has left in the tank have started to swirl ahead of this one.

Saint Denis debuted up a division at welterweight and lost, but since returning to the 155-pound ranks, the former French military man has posted five straight wins, all by way of finish, to climb into contention in the lightweight division. Last time out, the ascending 28-year-old walked into Matt Frevola’s backyard and knocked him out in front of a partisan crowd at Madison Square Garden.

UFC 299 COUNTDOWN: Full Episode | O'Malley vs Vera | Poirier vs Saint Denis | Holland vs Page 

This is a classic pairing between a tenured contender and one of the top emerging threats in the division, and it’s going to be fascinating to see how it plays out. Poirier has never been shy about going into battle, while Saint Denis possesses a relentless attacking style, so we should be treated to something special when these two step into the Octagon on Saturday night.

Kevin Holland vs. Michael Page

Kevin Holland welcomes Michael “Venom” Page to the Octagon for the first time in this welterweight clash that occupies the middle of the pay-per-view main card.

After dropping two straight to close 2022, Holland got things moving in the right direction again with consecutive stoppage wins over Santiago Ponzinibbio and Michael Chiesa to begin 2023 before dropping a split decision to Jack Della Maddalena at Noche UFC. The talented and free-spirited “Trailblazer” has already made 20 UFC starts and very few, if any, have not been entertaining, and this should be no different.

Order UFC 299: O'Malley vs Vera 2 

Page debuts in the UFC following an 18-fight run under the Bellator banner where he posted a 16-2 mark with each of his losses coming in championship fights. The Brit brings a unique style full of panache and showmanship into the cage at all times, and it will be interesting to see if he can still deploy the same approach now that he’s competing on the biggest stage in the sport.

Honestly, there is no predicting how this one plays out. You could tell me they’re going to breakdance fight on Saturday night and I couldn’t dismiss the possibility entirely. They’ll be jawing at each other from the outset — that’s a certainty — and the potential is there for this to be one of the most captivating fights of the year.

Gilbert Burns vs. Jack Della Maddalena

The second welterweight clash on the main card features Top 15 standouts Gilbert Burns and Jack Della Maddalena.

A South Florida resident, Burns earned a victory last spring in Miami, defeating Masvidal on his home turf. The former title challenger made a quick turnaround, competing a month later against Belal Muhammad, where he suffered a shoulder injury early and dropped a decision.

WATCH: O'Malley Sits Down With Megan Olivi Ahead Of UFC 299

Della Maddalena has earned three victories in each of his first two years on the UFC roster, capping last year’s campaign by getting the nod over Holland at Noche UFC. The 27-year-old Australian is unflappable in the Octagon, maintaining the same pace and demeanor in the early moments and late stages, whether things are going smoothly or not.

This one has a similar feel to the co-main event between Poirier and Saint Denis, in that we have a former title challenger looking to maintain his place in the pecking order facing off with an ascending competitor looking to collect the biggest victory of his career. Expect fireworks from this one.

Petr Yan vs. Song Yadong

Saturday’s main card kicks off in the bantamweight division, with former champion Petr Yan squaring off with emerging contender Song Yadong.

Yan touches down at UFC 299 in a precarious position, having dropped three straight and four of his last five, yet still standing as one of the unquestioned best in the 135-pound weight class. Narrow defeats to the last two champions and a loss to Merab Dvalishvili are nothing to hang your head about, however the 31-year-old needs a sharp performance to remind everyone of his elite status.

RELATED: Holland's Best Finishes 

Now in his seventh year on the roster and still just 26 years old, Song has amassed a 10-2-1 record inside the Octagon, including wins over Marlon Moraes, Ricky Simon, and Saturday’s title challenger, Marlon Vera. The talented Chinese competitor continues adding to his skill set and working forward in the rankings, and he can take another big step forward with a win here.

Can Yan work out of his slide and re-assert his standing as a perennial contender, or will this be the moment where Song stamps himself as a bona fide threat at the top of the bantamweight division?

Preliminary Card Fights

Curtis Blaydes vs. Jailton Almeida

The final preliminary card fight at UFC 299 is a high-stakes heavyweight battle between Curtis Blaydes and Jailton Almeida.

These two were scheduled to face off in November before Blaydes was forced to withdraw, resulting in Almeida thoroughly out-wrestling Derrick Lewis in Rio de Janeiro instead. Blaydes has been in the thick of the chase for a couple years, while “Malhadinho” has been ascending for the last couple years, and now they collide to determine who will hold a Top 5 ranking heading into the back half of 2024.

Katlyn Cerminara vs. Maycee Barber

Katlyn Cerminara and Maycee Barber meet in a pivotal flyweight matchup on Saturday’s prelims.

Cerminara (nee Chookagian) has been a fixture in the title picture for the entire duration of the division’s existence in the UFC, while Barber has been climbing the ranks on the strength of her five-fight winning streak. Will the stalwart turn back the prospect or is UFC 299 where Barber moves into title contention at Cerminara’s expense?

Mateusz Gamrot vs. Rafael Dos Anjos

Top 15 lightweights clash in this one as Mateusz Gamrot shares the Octagon with former titleholder Rafael Dos Anjos.

Gamrot earned a pair of wins in 2023, edging out Jalin Turner at UFC 285 in March before collecting a TKO victory due to injury in his main event pairing with Rafael Fiziev in September. Following a pair of welterweight appearances last year, Dos Anjos returns to the 155-pound weight class where he holds a 14-8 mark overall.

Pedro Munhoz vs. Kyler Phillips

The first of the night’s three bantamweight bouts features rankings mainstay Pedro Munhoz and TUF alum Kyler Philips.

The 37-year-old Munhoz has faced Top 15 competition for the majority of his UFC career, having faced O’Malley and Vera in two of his last three outings. Philips has quietly gone 5-1 through his first six UFC starts, entering on a two-fight winning streak.

Ion Cutelaba vs. Philipe Lins

Ion Cutelaba and Philipe Lins collide in what could be an explosive light heavyweight pairing early in the evening.

Cutelaba has been allergic to boring fights throughout his UFC career, while Lins has posted three straight victories since returning to the 205-pound ranks. Will “The Hulk” smash or will the Brazilian keep rolling?

Michel Pereira vs. Michal Oleksiejczuk

Michel Pereira and Michal Oleksiejczuk go toe-to-toe in a fascinating middleweight matchup on the prelims.

How To Watch UFC 299

Pereira looked sharp in his first UFC appearance at 185 pounds, stopping Andre Petroski in 66 seconds, while Oleksiejczuk has gone 3-1 with three stoppage wins since moving down in weight in 2022. Someone is getting finished in this one, and sorting out who that is should be all kinds of fun to watch.

Robelis Despaigne vs. Josh Parisian

Cuban Olympian Robelis Despaigne debuts opposite Josh Parisian in this heavyweight pairing.

A bronze medalist in taekwondo in 2012, Despaigne has gone 4-0 in MMA, with his two victories in 2023 coming in a combined seven seconds; yes, you read that correctly. Parisian arrives sporting a 2-4 mark inside the Octagon, aiming to lean on his experience in order to get things trending in the right direction again.

CJ Vergara vs. Assu Almabayev

DWCS grad CJ Vergara looks for a third straight win while Assu Almabayev targets a second UFC victory in as many starts in this intriguing flyweight fixture.

Vergara dropped two of his first three inside the Octagon, but has bounced back with consecutive victories over Daniel Lacerda and Vinicius Salvador. Almabayev debuted in August, posting a second-round submission win over Ode Osbourne to advance to 18-2 and extend his winning streak to 14 straight.

Joanne Wood vs. Maryna Moroz

Flyweight veterans open the show as Joanne Wood takes on Maryna Moroz in a rematch of a 2015 bout won by Moroz.

The 38-year-old Wood halted a three-fight slide with a split decision win over Luana Carolina at UFC 286 in London last March. Moroz dropped her second straight in her lone appearance of last year, tapping at the first-round horn in her UFC 292 clash with Karine Silva.