Max Holloway (Dave Mandel/Sherdog)

Toe-to-Toe: UFC 231 Preview and Predictions

On Saturday night, the UFC returns to the Scotiabank Arena, formerly the Air Canada Centre, in Toronto, Ontario, Canada, for the fifth time in the company’s history. The UFC 231 card features two title affairs.

The event is headlined by a featherweight title showdown between Hawaii’s Max Holloway and rising star Brian Ortega.

Holloway, the reigning champion, is currently riding a dominant 12-fight winning streak since his last loss to Conor McGregor over five years ago. McGregor went on to eventually secure the belt, but after he vacated, Holloway went on to defeat Anthony Pettis for the interim belt. The Hawaiian’s last two fights were back-to-back TKO stoppages of former champ José Aldo to solidify his standing at the top of the featherweight heap.


The California native Ortega is undefeated in his 15-fight pro career, and his top-contender status was solidified when he knocked out former lightweight champ Frankie Edgar in March. The 27-year-old Brazilian Jiu-Jitsu black belt will try to capture gold from a guy that waited a long time to get to the top, but has been on the bench for a full year.

The co-headliner pits Valentina Shevchenko against former strawweight champ Joanna Jędrzejczyk for the vacant women’s flyweight title, which was stripped from Nicco Montaño, who was hospitalized over complications in her weight cut and failed to show up for her first title defense against Shevchenko in August. This will be the first time Shevchenko and Jędrzejczyk have faced off inside the Octagon, but the two women have already met three times in the kickboxing arena. Shevchenko is considered the hands-down favorite, but Jędrzejczyk has champion’s blood.

The main card is rounded out with a welterweight battle between striker Alex Oliveira and grappler Gunnar Nelson, a featherweight fight between Canada’s Hakeem Dawodu and Boston’s Kyle Bochniak, and a light heavyweight bout with rankings implications as Jimi Manuwa faces former middleweight Thiago Santos.

The event kicks off with early prelims on UFC Fight Pass at 6 p.m. ET, before shifting to the preliminary card on Fox Sports 1 at 8 p.m. ET. The main card takes place on pay-per-view at 10 p.m. ET. Combat Press writers Matt Petela and Dan Kuhl preview the action in this edition of Toe-to-Toe.

Max Holloway was set to defend his featherweight championship against Brian Ortega in July, but he was forced out of the fight with concussion-like symptoms. Will Holloway still feel the effects of his health problems, or can we expect the same Holloway that has dominated the division?

Petela: Holloway will have been away from the Octagon for just over a year when he faces off against Ortega. In that time, he has had to withdraw from three fights, all for different reasons. First, his bout with Frankie Edgar was canceled a month before the contest when Holloway suffered a leg injury. Then, he volunteered to take on Khabib Nurmagomedov on a week’s notice at UFC 223 after Tony Ferguson destroyed his knee in a weird trip and fall accident while doing promotional work for the UFC. The New York State Athletic Commission pulled “Blessed” from the card due to the severity of his short-notice weight cut just a day before the fight. Then, there was his withdrawal from the first scheduled fight with Ortega.

As the July fight approached, Holloway seemed not to be himself. In a fight-week interview, Holloway’s responses were slow and groggy, prompting analyst and former middleweight champion Michael Bisping to ask him if he had just gotten out of bed. Shortly after the interview, Holloway was pulled from the card. His team and the UFC sought to discover the reason for the ailment, but it remains somewhat of a mystery. It’s been five months since the featherweight champion was affected with the concussion-like symptoms, and while there is no definitive cause, the attention that has been focused on Holloway’s health will ensure that the UFC and his fight team doesn’t allow him to step foot in the cage unless he is 100 percent ready.

So, if Holloway does get in the cage, he should bring all the skills and ability with him that he displayed on his rise to the featherweight title and subsequently defense of it in the rematch against José Aldo. However, even a full-strength Holloway won’t be able to come out with a victory over Ortega.

Ortega has finished all his opponents in the UFC. He has improved greatly with every fight, too. Ortega, a black belt in jiu-jitsu under Rener Gracie, relied almost solely on his grappling skills as he began his ascent toward the elite at 145 pounds. As time has passed, he has focused on his striking and proved he is dangerous on his feet as well. He became the first man to ever finish the aforementioned Edgar when he knocked out the former lightweight champion in the first round of their UFC 222 fight in March.

Holloway will have the advantage while the two men are on the feet, but the gap in striking will be far less than the distinct advantage Ortega has when the fight goes to the mat. “T-City” doesn’t have to rely on traditional takedowns in order to get the fight where he is most comfortable. He is dangerous off his back and is happy to pull guard if he is getting out-pointed, as he did against Cub Swanson. Ortega nearly submitted Swanson at the end of the first round before jumping guard and securing a guillotine while Swanson was standing with his back against the fence.

This could be the beginning of a long rivalry between Holloway and Ortega, both of whom are a few years away from turning 30. The belt will change hands, with Ortega ending the fight before the judges’ scorecards are necessary.

Kuhl: I wholeheartedly agree with my colleague’s assessment, but I’ll take it one step further.

Holloway got stuck in a really weird time and place in his career. After his loss to Conor McGregor in August 2013, he was truly climbing the ladder, but he had to go 10 wins in a row just to get a shot at an expired Aldo. Aldo was not the same fighter he was pre-McGregor. I’m in no way discounting Holloway’s wins, but he put a lot of miles on his chassis in four years — more than most — and now, arguably near his peak, he is having to face the new guy on the block, who is fresh and talented. Ortega has made a much shorter trek to the top, too. Of course, a lot of Holloway’s wait had been due to McGregor cleaning out the division, but miles are still miles.

Ortega, and the whole Black Belt Surfing thing, is the now. This guy hasn’t been to a decision in his four-year, seven-fight UFC career, and the only ding on his pro record was a no-contest due to a steroid pop in his promotional debut. Since then, he’s been doing what McGregor did in the couple years prior: picking apart the division. Ortega has been knocking out dudes, showcasing his Gracie jiu-jitsu, and proving that he will likely be the next UFC featherweight champ.

With Holloway’s general health in question, the Hawaiian’s title run appears bound to be short-lived. Ortega takes this one by stoppage prior to the championship rounds.

In the evening’s co-headliner, Joanna Jędrzejczyk and Valentina Shevchenko vie for the vacant women’s flyweight title. Will Jędrzejczyk, the former strawweight champ, find similar success at 125 pounds? Does she claim the belt in this fight?

Kuhl: This fight is a matchmaker’s dream. Granted, the matchmakers almost royally screwed the pooch. How they almost lost this fight to a Shevchenko and Sijara Eubanks headliner at UFC 230 is beyond me. No need to digress, though.

This is easily one of the most exciting match-ups of the year. Two of the world’s most successful champion kickboxers, who also happen to be two of the best MMA fighters, will collide in an unparalleled way. Both ladies are hungry as hell. They each lead a life consumed in fight training. They have faced each other three times in kickboxing already, with Shevchenko taking the win in all three bouts.

Shevchenko has a much deeper background, outside of just kickboxing. She has earned black belts and Master of Sports rankings in taekwondo, boxing, Muay Thai, kickboxing and, most importantly, judo. She’s got just as good striking as Jędrzejczyk, if not better, but she also has submitted seven opponents while tallying a total of 11 stoppage wins in MMA competition. This is a big difference from the Polish fighter, who everybody knows has great striking. Despite her skills on the feet, Jędrzejczyk has only knocked out four opponents in 15 pro wins, and it’s been more than three years since the last of those finishes

There’s also the size difference. Shevchenko has gone the distance, at bantamweight, with Amanda Nunes twice. She’s also heard the final bell against Holly Holm. Jędrzejczyk got knocked out by Rose Namajunas at strawweight, and she followed up that defeat with a lopsided decision loss in their rematch.

There will be a major power difference in this one. Shevchenko will come right out of the gate, take the fight to the former strawweight champ, and impose her will quickly. It’d be a surprise if this one makes it out of round two before Shevchenko stops Jędrzejczyk.

Petela: Jędrzejczyk is in a tough spot. She is possibly the greatest female Muay Thai fighter to step foot in the UFC, and yet this is not an area where she has a clear advantage in this contest. In fact, there isn’t any aspect of this bout where she will be more skilled than Shevchenko. The oddsmakers must agree, as they made Shevchenko a three-to-one favorite to win the vacant title.

However, it is not impossible for Jędrzejczyk to defeat Shevchenko. Her striking is lightning fast and comes with a sniper’s accuracy. The training and game plan she receives from Mike Brown and the rest of American Top Team will allow her to show up on fight night as the best version of her we have seen in the UFC, fully prepared and confident that she will leave with the belt and become the first two-division female champion in UFC history. However, the best Jędrzejczyk won’t be a match for Shevchenko.

Kyrgyzstan’s Shevchenko will be able to dictate whether this is a stand-up affair or a battle fought on the ground. If Jędrzejczyk can gain an advantage on the feet, then Shevchenko will be able to force the fight into the clinch and, ultimately, to the canvas. Jędrzejczyk’s takedown defense and scrambling abilities won’t be enough to outweigh Shevchenko’s judo, and the Polish former champion will find herself in the worst place possible, on her back with Shevchenko on top of her looking to either turn off the lights with ground-and-pound or snatch her neck and force the former strawweight to submit.

This one doesn’t end well for Jędrzejczyk. It will make for an easy decision to move back down to 115 pounds for the rest of her UFC career.

Beyond the double feature of championship affairs, the UFC has lined up a pair of contests between fighters who are on the edges of true contendership in their respective divisions. At light heavyweight, former middleweight Thiago Santos takes on Jimi Manuwa, who has suffered back-to-back losses. Meanwhile, surging welterweight Alex Oliveira tries to get past Gunnar Nelson. Will either Santos or Oliveira make a convincing statement at UFC 231?

Petela: When Santos defeated Eryk Anders, it was hard to imagine how he ever fought at middleweight. He was certainly depleting his body by cutting the extra 20 pounds, and he looked big as a light heavyweight. If we look at the fight in a vacuum, then Santos looked crisp and appeared to have the ability to compete with the best in the world at 205 pounds. However, Anders took the fight on six days’ notice, and he, too, was moving up in weight, so it’s hard to believe this was the best version of the former University of Alabama linebacker. That doesn’t mean Santos won’t be a force to be reckoned with in his new division, but it’s too soon to tell.

It was due to a last-minute training injury for Manuwa after arriving in Brazil that Anders was afforded the opportunity to step in against Santos. The British fighter has his back against the wall in this rescheduled contest. Manuwa did not look impressive in his last two fights, where he was knocked out in the first minute against Volkan Oezdemir and dropped a unanimous decision to Jan Blachowicz. The Blachowicz fight earned “Fight of the Night” honors, but the victory was never in doubt for Blachowicz, who wobbled Manuwa and looked like the much crisper man in the striking department. The 38-year-old Manuwa is closer to the end of his career than the beginning, and a loss against Santos might prove to be his final bout in the UFC.

Unfortunately for Manuwa, Santos will prove he is a real contender at light heavyweight. Santos will force the fight to take place in a phone booth and show off the power in his hands at the higher weight class. The Brazilian will land devastating punches in close range that turn out the lights for Manuwa, not only on his fight night but on his UFC career as well.

Oliveira has looked great in his last five fights, going 4-1 over the span with the only loss coming in an unforgettable fight against Yancy Medeiros at UFC 218. After having Medeiros in serious trouble earlier in the fight, Oliveira suffered a TKO loss while still earning a “Fight of the Night” bonus. Since then, Oliveira has looked even better. He submitted former interim titleholder Carlos Condit and then made short work of Carlos Pedersoli with a 39-second knockout.

The Brazilian will likely look to keep the fight standing against Nelson to try to avoid getting tangled up on the ground with the standout grappler from Iceland. Nelson is trying to prove he still belongs amongst the best at 170 pounds. While there was some controversy regarding an eye poke in his first-round TKO loss to Santiago Ponzinibbio, the fight took most of the steam away from Nelson, who was coming off his first back-to-back wins since 2014.

Oliveira and Nelson are both 30 years old, and they will both likely go on to have several more fights. However, it will be Oliveira who does so against the top of the welterweight division, while Nelson becomes a formidable, though beatable, gatekeeper for the remainder of his time with the promotion. Elusive striking and takedown defense will be the story of this fight, as Oliveira runs away with a decision victory.

Kuhl: It’s funny to think of Oliveira trying to “get past Gunnar Nelson.” Nelson’s only major strength is grappling, and he’s damn good at it, even in MMA. However, he’s going to have a major reach disadvantage against a striker with devastating power who also happens to be a good submission grappler. Now, make no mistake, Oliveira’s jiu-jitsu is nowhere near the level of Nelson’s outside the cage, but all fights start standing, and it wouldn’t be a surprise to see Nelson get knocked out.

As far as Santos and Manuwa, my colleague is right. Manuwa is starting to battle Father Time, as was pretty apparent in his last two fights. Anybody who can manage to knock out Ovince Saint Preux has obvious power, but that knockout happened two years ago.

Meanwhile, Santos has quietly been following in the footsteps of his former foe, Anthony Smith. Smith is on his own meteoric rise, but a move up to light heavyweight was the best decision he’s ever made. Well, Santos has already defeated Smith once at middleweight. A win over Manuwa could very well launch him into the top 10 at 205 pounds. How sweet would it be for him to get a shot at Smith again for the light heavyweight title? Of course, a lot would need to happen for that to take place, but it’s not impossible. The path for Santos starts with a win over Manuwa, which is a very real possibility. Santos could win this one standing, but he would almost be guaranteed a win on the ground.

Who’s the biggest winner at UFC 231?

Kuhl: Here’s a name you haven’t heard in a while: Jesse Ronson. This is a golden opportunity for a guy that really only washed out of the UFC on paper. Three split-decision losses, with the last one coming to Kevin Lee in 2014, is not the worst showing. After that, he won two, before going on another three-fight skid. However, when two of those losses are to fellow UFC vet Matt Dwyer and Bellator, M-1 and Absolute Championship Berkut vet Alexander Sarnavskiy, both by decision, again, it’s not the worst thing ever.

Ronson has gotten back on track with four stoppage wins in a row, and he has stopped 16 opponents, while only being stopped twice. John Makdessi, who is on a two-fight winning streak, was set to face Carlos Diego Ferreira, who is also on a two-fight streak, but Makdessi had to pull out, and Ronson, an Ontario native who was in the right place at the right time, got the call with just over a week’s notice. Even if Ronson loses, he most likely got a multi-fight deal, and, as is usually the case with these, they will probably put him right back to work. If he wins, that’s just icing on the cake. It’s a win-win for the Canadian, who will be fighting on his home turf.

Petela: Kyle Bochniak. The Massachusetts fighter gets his second consecutive main card on a pay-per-view this weekend when he takes on Hakeem Dawodu. Bochniak faces a hostile crowd when he squares off against the World Series of Fighting veteran, who happens to hail from Canada.

In a losing effort to the UFC’s biggest prospect in some time, Zabit Magomedsharipov, Bochniak saw his popularity and stock rise in a “Fight of the Night” performance. Dawodu is an accomplished kickboxer with 55 combined amateur and professional kickboxing bouts before making the switch to MMA. This should be another fight that brings fans to their feet, and this time Bochniak will leave with a victory that keeps him fighting in high-profile events as much more than someone to use to showcase up-and-coming talent at featherweight.

Who’s the biggest loser at UFC 231?

Petela: Joanna Jędrzejczyk. Unfortunately for the seemingly unstoppable former strawweight champion, a loss to Shevchenko would be the third loss in her last four fights, all which will have come in championship contests, and her path to reclaiming UFC gold will become quite daunting.

The 115-pound division that Jędrzejczyk once owned has seen a tremendous influx of contenders who are all world-class mixed martial artists. Between her two losses to current champ Rose Namajunas and the rise of fighters like Tatiana Suarez and a resurgent Jessica Andrade, who is on a three-fight winning streak after dropping her first shot at the title to Jędrzejczyk, there is no clear-cut path back to a title shot for the Polish Muay Thai legend. Furthermore, a rematch with Shevchenko is not a likely option if she drops the shot at the vacant belt.

This will be the fourth combat-sports competition between the two Eastern European destroyers, who met three times previously in Muay Thai fights. Those contests took place a decade ago, so to think either woman is the same fighter or that Muay Thai results would directly translate to MMA results would be foolish. Still, a loss to Shevchenko would put Jędrzejczyk in the middle of the flyweight pack, with several fighters in the division able to boast somewhat valid arguments as to why they should be the next person in line for a title shot.

This list includes UFC 231 prelim fighters Katlyn Chookagian and Jessica Eye. The winner of that fight will have a 3-0 record at flyweight in the UFC, a notable accomplishment in the UFC’s newest division. While a loss to Shevchenko won’t be a career-ender, it will be career-altering for Jędrzejczyk, who will have to take out some stiff competition over several fights if she is to earn a third chance at a championship.

Kuhl: I’m not feeling great about the aforementioned Eye’s position in this one. She was, technically, 2-5 in the UFC — one split-decision win was overturned to a no-contest after Eye tested positive for THC — but, after coming off four losses in a row, she’s had back-to-back wins. However, one of those victories came over Kalindra Faria, who is winless in three appearances in the Octagon.

Eye’s opponent for this one, Chookagian, is in a completely different boat. She is 4-1 in the UFC and has won three in a row. Her last victory came against Alexis Davis, who has notable wins over some of the highest ranked fighters in the world. Eye has had a lot of chances to prove she belongs in the UFC, but her time is almost up. She has a tough opponent who she is not likely to beat, and it seems like this will put her in a bad spot with her current employer.

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

Kuhl: Eryk Anders and Elias Theodorou. The former is an NCAA Division I college football champion who has a penchant for knocking the shit out of people. The other is a Canadian hair model and The Ultimate Fighter winner who has dragged guys like Sam Alvey and Trevor Smith into deep waters for dominant decision wins, but who has also knocked out a few UFC opponents along the way. This should be a fun fight with some drubbings as well as some grappling. If it does go the distance, these guys should look bloodied and battered by the final bell.

Petela: Claudia Gadelha and Nina Ansaroff. It might be headlining the prelims, but there is not enough buzz surrounding this contest.

Gadelha has been at the top of the strawweight division since its inception. She is coming off a victory over the division’s first champion, Carla Esparza. The only losses on Gadelha’s record came against Joanna Jędrzejczyk (twice) and phenom Jessica Andrade, who should be the next contender for the title.

Ansaroff, on the other hand, is best known as Amanda Nunes’ fiancé. She has quietly gone on a three-fight winning streak after dropping her first two UFC appearances. Gadelha should be able to claim another victory at 115 pounds that will put her name firmly in contention for another crack at the belt now that Rose Namajunas reigns as champion. However, it might take one more fight after this for Gadelha to get back to a title shot with the aforementioned Andrade and streaking Tatiana Suarez both having earned their way to legitimate contender status. Gadelha, who celebrates her 30th birthday just a day before this event, will be a threat at strawweight for years to come.

Pair this card with…

Petela: An “Eye Believe” t-shirt. Cleveland’s Jessica Eye takes on Katlyn Chookagian in a women’s flyweight fight that should see the winner advance to next in line for a chance at the 125-pound title. Chookagian is a brown belt in jiu-jitsu under Renzo Gracie and will be far from an easy task for Eye, but expect Eye’s crisp offensive striking and elite striking defense to make the difference in the fight. There will be a post-fight call for a shot at the belt, one that will be well deserved for Eye.

Kuhl: My shirt will say “Eye Doubt It.” I really like Eye as an elite fighter, but history doesn’t lie. She has had trouble pulling off a really dominant win over a high-level opponent, and her No. 9 ranking is more of a result of the current depth of the new division. Chookagian, on the other hand, is coming in with a full head of steam, a dominant win over Alexis Davis, and a chance at a title with a win over Eye. Chookagian will be victorious.

Fight Picks

Fight Petela’s Pick Kuhl’s Pick
Main Card (Pay-per-view, 10 p.m. ET)
FW Championship: Max Holloway vs. Brian Ortega Ortega Ortega
Women’s FlyW Championship: Joanna Jędrzejczyk vs. Valentina Shevchenko Shevchenko Shevchenko
LHW: Thiago Santos vs. Jimi Manuwa Santos Santos
WW: Alex Oliveira vs. Gunnar Nelson Oliveira Oliveira
FW: Kyle Bochniak vs. Hakeem Dawodu Bochniak Dawodu
Preliminary Card (Fox Sports 1, 8 p.m. ET)
Women’s StrawW: Claudia Gadelha vs. Nina Ansaroff Gadelha Gadelha
Women’s FlyW: Jessica Eye vs. Katlyn Chookagian Eye Chookagian
MW: Eryk Anders vs. Elias Theodorou Anders Anders
LW: Gilbert Burns vs. Olivier Aubin-Mercier Aubin-Mercier Burns
Preliminary Card (UFC Fight Pass, 6 p.m. ET)
LHW: Aleksandar Rakic vs. Devin Clark Clark Rakic
BW: Brad Katona vs. Matthew Lopez Lopez Katona
WW: Chad Laprise vs. Dhiego Lima Lima Laprise
LW: Carlos Diego Ferreira vs. Jesse Ronson Ferreira Ferreira