UFC 299 Predictions

UFC 299 takes place tomorrow night in Miami, Florida and we’ve got our predictions for all the fights below.

Main Card

Sean O’Malley vs. Marlon Vera

O’Malley and Vera fought for the first time in 2020 and it was Vera who emerged victorious with calf kicks early on severely compromising his opponent’s movement, paving the way for a TKO finish before the end of the round. O’Malley has insisted that was just a fluke and has since gone on a six-fight winning streak, winning the bantamweight title along the way, while Vera has put together a 5-2 run and picked up a decision win over Pedro Munhoz last time out.

The 29-year-old comes into this fight high on confidence as you might expect from someone who has proven to be a gifted striking talent during his rise to become champion. He has very good technique, manages distance well with good footwork and has proven power, but what really sets him apart on the feet is his razor-sharp timing and accuracy, which together with his speed and ability to read his opponents has proven to be a deadly combination. As such he has fight-ending ability with his punches in particular, though his head kicks are also a major threat. On the downside his lack of defense against leg kicks is a big concern, while he’s never been beyond the third round in a fight before and we’ve still to see his ground game fully tested.

The 31-year-old Vera’s early finish against O’Malley wasn’t his usual M.O. as he’s typically a slow starter who builds as the fight goes on. When he does build up a head of steam he can be very dangerous though and has notched up impressive finishes in the later rounds, including third round head kick stoppages of Frankie Edgar and Brad Pickett along with a fourth round finish against Dominick Cruz. So it’s not just leg kicks that O’Malley has to be concerned with as Vera will also attack upstairs with them, and has good punches too. While Vera’s highlight-reel finishes have grabbed the most attention it shouldn’t be forgotten that he’s also a very good grappler and has more finishes via submission than strikes, and of course he’s also known for being very durable, having never been finished in his career.

That being said, a real concern for Vera heading into this fight is that he’s actually underperformed in recent fights, seeming to struggle to shift gears and make full use of his offensive weapons in the later rounds after his usual slow start. There’s also been talk that he’s had a bad camp leading into this fight, though it’s hard to know if there’s any real truth to that.

Still, while Vera has more than one way to win here I do have concerns for him if the calf kicks that worked so well for him last time out don’t have the same swift and catastrophic effect this time around. Vera isn’t the most defensively sound and does lean on his durability, so there will be plenty of opportunities for O’Malley to land here, and with his power and precision I think that he takes the lead early here and hands ‘Chito’ his first loss via strikes via TKO in the second round.

Pick: Sean O’Malley wins by TKO in Rd2

Dustin Poirier vs. Benoit Saint Denis

Dustin Poirier has fought for titles in two of his last three fights, but came up empty-handed, suffering a submission loss to Charles Oliveira in their 155lb title clash, while also being KO’d by Justin Gaethje in their clash for the symbolic ‘BMF’ belt. Poirier then called for another big name opponent next, but somewhat surprisingly instead settled for a rising star in Benoit Saint Denis, who is making waves with wins in his last five UFC fights.

The 35-year-old Poirier has started to entertain talk of retiring recently, admitting that while he’s not planning to hang up his gloves just yet, there is the possibility that any fight could be his last. Nevertheless, heading into his 30th fight in the UFC Poirier still remains ranked No.3 at 155lbs for good reason, bringing experience and expertise to the Octagon with his well-honed striking ability. He’s always been willing to get into a war, but he remains a strategic striker in the firefight and puts together his combinations with purpose and good power. He’s still well-conditioned too, but at this stage in his career and coming off a head kick KO loss durability will be a concern. Meanwhile, though he’s a highly-capable all-rounder his takedown defense isn’t impenetrable and does have a few submission losses on his record.

The 28-year-old Saint Denis is known as ‘The God Of War’ and certainly shows in his fights as he is a pwerful, athletic fighter who is eager to wade into battle, leading the charge with thumping kicks and hard-hitting punches that has worked out well for him of late with three wins via strikes in his last four fights. It is a style that favors offense over defense, which is always a risk, but he’s demonstrated a strong chin so far and has never been stopped inside the distance. Meanwhile, BSD benefits from a multi-pronged approach as he’s also a good wrestler and used submissions to beat the majority of his opponents on the regional circuit – something he’s replicated in the UFC a couple of times too.

It feels like a fight where Poirier has more to lose than gain at this stage when he’s seemingly questioning how much longer he wants to compete. Perhaps he sees Saint Denis as still a little rough-around-the-edges and lacking five-round experience. Poirier does seem more crafty in the striking department, but I think the younger, hungrier BSD’s more brute-force approach, backed up by his durability and good grappling will serve him well and lead to a third round TKO victory.

Pick: Benoit Saint Denis wins by TKO in Rd3

Michael Page vs. Kevin Holland

One of Bellator’s best homegrown-stars, Michael ‘Venom’ Page earned a TKO victory in his final fight for the promotion and now finally makes the move over to the UFC where he’ll debut against Kevin Holland, who won his first two fights last year, but then lost out by split-decision to Jack Della Maddalena.

The 36-year-old Page joined Bellator very early in his career and went on to compile a 17-2 record there, though despite his star status he was unsuccessful in his only title fight there. Still, even at this relatively late stage in his career it’s good to see him in the Octagon as he’s always been a highly talented, athletic and very dynamic striker who is capable of stunning highlight-reel finishes. Tall and lengthy, yet fast and agile, Page is perfectly suited to his ‘Venom’ nickname as he lures foes into a false sense of security with his unorthodox movement on the outside, but can then strike with a fight-ending punch, kick or knee out-of-the-blue. Page’s ground game will be a concern heading into the UFC’s welterweight ranks though as in Bellator he was given a relatively easy ride in terms of stylistic matchmaking.

It’s not hard to see why the UFC were keen to put Holland up against Page as he is also a showman with confident, dynamic and creative striker with proven finishing power. He also matches up well to him size wise, and in fact actually has an extra 2″ in reach and a build that supported an extended middleweight run before dropping down to 170lbs. That move down in weight was prompted by struggles against strong wrestlers, but that’s not going to be an issue against Page and Holland is actually a capable offensive wrestler with respectable submission ability.

Of the two I’d say ‘Venom’ is the more cold, calculated striker despite his flashy style. With Holland being more impulsive and impressionable that does makes me a little hesitant to pick him. Even so, I do feel that Page finds himself in an unusual situation here in that he’s facing someone that’s similarly sized and is also fast, dynamic and dangerous like he is. Holland’s reach may also make it more tricky for ‘Venom’ to operate as effectively as usual, and if ‘Trailblazer’ makes use of his ground game then that’s going to be a major headache for him too. With that in mind I’ll take Holland to win by decision.

Prediction: Kevin Holland to win by decision.

Gilbert Burns vs. Jack Della Maddalena

Last year Gilbert Burns won two fights in a row but then lost out by decision to Belal Muhammad. Now he fights Jack Della Maddalena, who gone unbeaten in the UFC so far with wins in all six of his fights.

At 37-year-old Burns is at that stage where signs of decline are a real concern, but while he struggled with a shoulder injury in his last fight he generally appears to be aging gracefully. A former title contender, Burns has a lot of experience under his belt and a very well-rounded skill-set too. As a former lightweight he’s not the biggest 170lb’er, but he’s proven to be strong and durable for his size in the division and pushes a hard pace. His strongest suit is his very high-level grappling ability, but Burns has solid wrestling too and has no problems mixing things up on the feet, showing no fear with his pressure-based style and he does pack a punch.

Maddalena is a full decade younger than Burns at 27-years-old. He’s known for his gritty striking style, showing a willingness to get into close quarters and unleash tight, compact boxing combinations to the head and body that resulted in his first three UFC opponents being stopped inside the first round. He then showed off some submission ability with another 1st round finish against Randy Brown, but he’s found the going tougher in his two fights since, having to settle for split-decision wins over Bassil Hafez and Kevin Holland.

Perhaps this is the fight where Burns will start to feel his age, but even though Maddalena’s a real striking threat I suspect that this is another fight where he isn’t going to just be able to run through an experienced, durable veteran. Instead he’ll have to work hard for it, and if he is able to keep it upright then he stands a good chance. However, Burns will hold his own to an extent on the feet and will have a significant advantage if he’s able to get the fight to the mat. And with his pressure and doggedly determined approach I do feel he will be able to get Maddalena down at times. From there a submission finish is a real possibility, and if not then it’ll still set him up to win on the scorecards.

Pick: Gilbert Burns wins by decision.

Petr Yan vs. Song Yadong

Petr Yan’s enjoyed a dominant rise to become bantamweight champion in 2020, but remarkably he’s gone on to lose four out of five fights since and now has another big challenge in front of him against Song Yadong, who is 4-1 in his last five Octagon appearances.

The 31-year-old Yan’s recent record isn’t all it seems though. He title loss to Aljamain Sterling was due to landing an illegal knee in a fight he had been winning, leading to a DQ. Then came an interim title win over Cory Sandhagen, while his subsequent losses to Sterling and Sean O’Malley both came via narrow split-decision verdicts. Admittedly he did lose fair-and-square to Merab Dvalishvili, but that’s a fate many have shared in recent years.

The upshot is that Yan hasn’t lost it, but he is now under a lot of pressure to prove that he’s still part of the elite at 135lbs. Yan is a very skilled boxer who operates behind a high guard and applies a lot of calculated pressure, looking for weaknesses to exploit and attacking with speed, power and volume when the opportunity presents itself. He also has good cardio, still remains unfinished inside the distance and for the most part has had very solid takedown defense and can work back to his feet nicely when required.

Having entered the UFC at a young age with promising ability but a slightly patchy record, the now 26-year-old Yadong has done well to not only survive in the Octagon, but thrive while further honing his skills and is now looking to break into the bantamweight Top 5. He’s a talented technician on the feet with good boxing with both speed and notable power in his punches, while he will also feed solid kicks into his attacks too. He’s also well-conditioned, stays composed defensively and can mix in some offensive wrestling too.

This is a well matched, intriguing fight that could go either way. Yadong may benefit from from more of a willingness to use kicks and of course he has momentum on his side. However, in a hard-fought tactical battle I favor Yan to be more effective at applying pressure, making good reads during the heated exchanges and also feel he is the one more likely to be able to land a couple of takedowns too to help edge out an extremely close decision victory.

Pick: Petr Yan wins by decision.

Prelims

Curtis Blaydes vs. Jailton Almeida
Katlyn Chookagian vs. Maycee Barber
Mateusz Gamrot vs. Rafael dos Anjos
Pedro Munhoz vs. Kyler Phillips
Michel Pereira vs. Michal Oleksiejczuk
Ion Cutelaba vs. Philipe Lins
Robelis Despaigne vs. Josh Parisian
CJ Vergara vs. Assu Almabayev
Joanne Wood vs. Maryna Moroz

Ross Cole
Ross launched MMA Insight (previously FightOfTheNight.com) in 2009 as a way to channel his passion for the sport of mixed martial arts. He's since penned countless news stories and live fight reports along with dozens of feature articles as the lead writer for the site, reaching millions of fans in the process.