It was just over 12 years ago when Demian Maia made his debut at UFC 77, where he scored a rear-naked choke victory over Ryan Jensen. The Brazilian has gone on to rack up nine more submission wins, tying him with Royce Gracie for the second most submissions in UFC history. Now, at UFC on ESPN+ 20, Maia, an ADCC gold medalist, looks to pick up a third consecutive win after falling on hard times and dropping three straight bouts for the first time in his career.

Maia takes on fellow world-class grappler and Olympic freestyle wrestler Ben Askren in a five-round welterweight main event. Askren is coming off his first professional MMA loss, a record-setting five-second knockout courtesy of a Jorge Masvidal flying knee. It will be a homecoming of sorts for Askren, who, prior to signing with the UFC in a landmark trade, competed under the Singapore-based ONE Championship banner and reigned as the promotion’s welterweight champion.

The deep talent in the lightweight division will be on display in the evening’s co-headliner when Michael Johnson meets Stevie “Braveheart” Ray. This will be Johnson’s return to 155 pounds after an underwhelming 2-2 stint at featherweight. Johnson had aspirations at making a championship run at 145, but now the 33-year-old will need to deliver an impressive performance against Ray to reclaim his relevance as a legitimate threat to the contenders in the stacked lightweight division. Scotland’s Ray is also looking to right the ship after dropping three of his last four contests. Ray made his professional debut in a short-notice fight in 2010 where he competed as a middleweight before dropping to welterweight for his next seven bouts and ultimately finding a home at lightweight in 2012. Despite his time in heavier weight classes, Ray gives up more than three inches in reach to his opponent and fellow southpaw.


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Further down the lineup, lightweight fighter Beneil Dariush takes on Frank “The Crank” Camacho. A black belt in Brazilian Jiu-Jitsu under Romulo Barral, Kings MMA’s Dariush is coming off a “Performance of the Night” triangle armbar over Drew Dober. Camacho is a notoriously heavy-handed boxer who has 17 wins by knockout and has collected three “Fight of the Night” bonuses in his five UFC appearances. The first of these bonuses came when Camacho made his promotional debut and dropped a unanimous decision to Li Jingliang in the same arena where he will meet Dariush.

Lightweight is the deepest division in the UFC, but welterweight is a close second, as evidenced not only by the main event but also by the fight between Muslim Salikhov and Laureano Staropoli. Salikhov, who is fighting for the fourth time in the UFC, is a 199-fight kickboxing veteran and one of only two non-Chinese men to win the Wushu Sanda King’s Cup. Staropoli makes his third Octagon appearance after picking up unanimous decisions in his freshman and sophomore outings. If Salikhov wants to become a title contender, the time is now. The Dagestani striking ace is entering the back side of his 30s, and a third consecutive knockout could go a long way in the eyes of UFC matchmakers. Staropoli, 26, is nine years younger than Salikhov and will have a slight one and a half inch reach advantage, which he will look to utilize to keep the fight at his preferred long-range striking distance to avoid the thunderous punches of Salikhov.

UFC on ESPN+ 20 will mark the third consecutive year that the world’s premier MMA organization holds an event in Singapore. The Singapore Indoor Stadium in Kallang will be the host venue and, like previous UFC events, the festivities kick off bright and early for the North American crowd. Preliminary bouts will get underway at 5 a.m. ET on ESPN+, to be followed at 8 a.m. ET by the main card, also available on ESPN+. Combat Press writers Dan Kuhl and Matt Petela preview the action in this edition of Toe-to-Toe.

Ben Askren hasn’t exactly impressed since arriving in the UFC. Does that change when he meets Demian Maia?

Kuhl: Obviously, Askren’s win over Robbie Lawler in his UFC debut was a bad stoppage, but he had a tight bulldog on a guy whose only other submission losses in the last decade came to Ronaldo “Jacare” Souza and Jake Shields. Just to have Lawler in that precarious position that early in the fight was pretty impressive. Askren’s undefeated record prior to his arrival in the UFC didn’t exactly come against a bunch of tomato cans, either. He lost his second UFC appearance to Jorge Masvidal in five seconds by a flying knee, but that was a combination of bad planning, timing, and luck. It was certainly not indicative of Askren’s Octagon future. Just ask Maia.

The Brazilian suffered his first career loss in the Octagon a decade ago, when Nate Marquardt blasted him off of his feet in just 21 seconds. However, after the loss, Maia was not stopped again in his next 16 fights. He has beaten or gone the distance with some of the best in the game. The UFC has not seen the best Askren has to offer the welterweight division.

Maia is 41 years old; Askren is 35. Askren has more striking power than Maia, and he sets up bad situations — like the one he put Lawler and all of his other previous opponents in — with his amazing wrestling. Maia’s striking style is not to come in with a flying knee. The grappling ace prefers to strike at a distance, until he can set up his best-in-class jiu-jitsu attack. This is where the conundrum lies: both men want their opponent on the ground. While Maia is comfortable on the bottom, Askren wants to be on top. At this point, it’s a war of attrition.

Askren is younger and more powerful. Maia will likely not be able to sustain enough of the wrestler’s attack to set up a quality submission in time, so Askren takes this one by stoppage before the midpoint of round two.

Petela: What has stood out the most about Askren since his signing with the UFC is how well he has handled the knockout loss to Masvidal. He didn’t hide from the media or fans on social media like Ronda Rousey did after the Holly Holm fight. He didn’t make excuses like Karo Parisyan, who hilariously claimed that the reason he lost to Thiago Alves was because he was too talented to train. Instead, Askren did an interview just three days after the loss and refuted fans’ claims that Masvidal got lucky. So, while his time inside the Octagon could have certainly gotten off to a much better start, he has shown the type of character that is almost as important as talent and game plan in order to succeed at the highest level.

Askren will be able to finish the fight inside the distance. In that regard, his performance will be impressive. We have seen numerous times that when two championship-caliber grapplers meet, the fight turns into a kickboxing match where neither man wants to play into their opponent’s strength. Unfortunately, the striking display will be a far cry from the level we saw between Jacare and Chris Weidman. Souza, like Maia, is a grappler, whereas Weidman and Askren are both former NCAA Division I All-American wrestlers. The match-up in Singapore will probably look like a slow motion version of the Jacare/Weidman contest until it does eventually get to the canvas.

Maia really isn’t afraid to fight off his back, but his real forte is in his conventional jiu-jitsu. He doesn’t have the unorthodox style of Ryan Hall, but rather uses the core principles and techniques of Gracie jiu-jitsu. He methodically advances into increasingly dominant positions, secures back mount, and forces a submission, most frequently by rear-naked choke or neck crank. However, Maia won’t be able to take Askren down, nor will he be able to pull guard and sweep the two-time NCAA champion. If and when Maia is forced to pull guard, he will have exhausted too much energy trying to secure a takedown and will succumb to Asken’s infamous ground-and-pound.

The lineup also features a pair of welterweights that have largely flown under the radar despite posting multiple UFC wins. Who breaks out in this affair, Muslim Salikhov or Laureano Staropoli?

Petela: Salikhov, though admittedly there might be some recency bias in this pick.

Salikhov looked great in his first-round knockout of Nordine Taleb just a month and a half ago at UFC 242 in Abu Dhabi. The 35-year-old Wushu Sanda world champion is a finisher who has only seen the judges’ scorecards once in his 15 professional victories, including two consecutive knockouts inside the UFC.

Staropoli isn’t going to be a cakewalk for Salikhov, though. The Argentinian striker is riding a seven-fight winning streak and has yet to taste defeat since joining the UFC. He outpointed Thiago Alves in Brazil at UFC 237 and showed off a wide variety of strikes en route to a unanimous-decision victory.

It’s hard to know for sure how much stock to put into each man’s most recent fight. They both took on grizzled veterans who are closer to 40 than they are to 30 and who have each lost three of their last four fights.

This fight comes down to Salikhov’s ability to combine precision with power, whereas Staropoli hasn’t shown the same type of fight-ending power at the highest level of the sport. His UFC debut was a slugfest with Hector Aldana where Staropoli landed 97 significant strikes and had Aldana bleeding within the first 60 seconds. He couldn’t close the show against his Mexican opponent, though.

This should be a high-level striking showcase, with Salikhov getting his third consecutive knockout and snapping Staropoli’s winning streak.

Kuhl: Given what Salikhov and Staropoli have done in their past fights, it’s really hard to gauge how this fight will unfold.

Both men have indeed fought aging journeymen, as well as record-padding opponents. Argentina’s Staropoli has fought much less-experienced competition, however, and hasn’t exhibited a ton of stopping power in the Octagon. Salikhov, meanwhile, finishes fights.

Both of these men have a lot to prove, and their pre-UFC records do not carry a lot of weight. My money is on the Russian fighter for this one.

Dontale Mayes and Loma Lookboonme — do we need to know these names?

Kuhl: Lookboonme might be new to the Octagon — and to MMA as a whole — but the 23-year-old striker already has a long history of competition in combat sports. She’s been fighting since she was only 16. From May 2011 to October 2014, she went undefeated across 17 fights. This came after she started with a 2-3 record. In MMA, she has only lost once, via first-round armbar submission nearly a year ago. She is still young and needs to discover her true potential in the MMA world. She won’t best Aleksandra Albu on Saturday, but crazier things have happened.

I, admittedly, don’t know as much about Mayes. He had a long, undefeated career as an amateur, and we’ve seen him three times now on Dana White’s Tuesday Night Contender Series Contender Series. He lost his first one to Allen Crowder, but his next two fights on the show ended in TKO stoppages, both in his favor. Mayes is definitely a striking-oriented fighter with a lot of power, and Cyril Gane will be a good test to see how he may fare against an undefeated opponent who already has a win in the Octagon.

Petela: It seems like Mayes is in over his head against Gane. He does certainly have the edge in experience, but he is going up against a more versatile fighter who has finished all four of his professional wins. Gane has two victories by knockout and two via submission, including an arm-triangle choke in his own UFC debut. Heavyweight fighters typically peak later than those in other weight classes, so it’s feasible to think that Mayes, 27, has not entered his prime yet. However, his lengthy amateur career makes him close to a finished product. His skills aren’t on par with even the middle tier of UFC heavyweights.

Lookboonme, a former atomweight, is actually moving up in weight for her UFC debut. She meets Albu at strawweight, but the Tiger Muay Thai product won’t have much success in Singapore. Her frame, combined with her background as a striker, will halt her from progressing into a mainstay in the UFC. She stands 5-foot-1, which is two inches shorter than Michelle Waterson, and the two share a 62-inch reach. In nearly every strawweight fight, Waterson, who thrived as an atomweight, has been at a height and reach disadvantage. The path forward for Lookboonme is at 105 pounds. Until the UFC adds the weight class, her future is best spent outside the promotion.

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

Petela: It should be easy to come up with a joke about how they’re all sleeper fights for fans in North America, but I’ve got nothing. The strawweight showdown between Randa Markos and Ashley Yoder is a fight worth getting up early to watch, though.

Since dropping her first three UFC fights, Yoder has rebounded nicely to pick up wins over Amanda Cooper and Syuri Kondo. This puts her within one victory of a .500 record inside the Octagon. Markos has alternated wins and losses over her 12 UFC fights, adding a draw with Marina Rodriguez. She will also be looking to get back to .500, with her current promotional record standing at 5-6-1. It’s unlikely we will see a knockout from these fighters, neither of whom has recorded a professional knockout so far. These women are talented grapplers with multiple submission wins on their records, and this should be the perfect appetizer for the main event.

Kuhl: Lookboonme and Albu will engage in an exciting fight that people who don’t follow women’s MMA closely will not be expecting. Both of these ladies are tremendous athletes, and while Lookboonme will give up some size and strength, her striking skills are light years ahead of Albu. This fight is super important for both ladies, and they are hungry for an Octagon victory.


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Pair this card with…

Kuhl: A dozen beers from a dozen different countries — the same as the number of countries represented in the lineup. With fighters from all over the world in all different stages of their careers, this card is shaping up to provide something new and exciting with every single bout.

Petela: Death Wish coffee and Melatonin, but not simultaneously. The start time is 5 a.m. on the East Coast, which isn’t ideal. Those in the Mountain and Pacific time zones have it much worse. So, to make sure you are awake and able to catch this event in its entirety, have a cup of Death Wish coffee half an hour prior to coverage. There’s an insane amount of caffeine, so you’ll be set for several hours. The Melatonin comes in handy for when the caffeine has worn off and you’re becoming too tired to fall asleep. Take the Melatonin just as the headlining fighters are being introduced — not long after the conclusion of the fight, you’ll be dozing off for a mid-day nap that leaves you refreshed and ready for your Saturday-night plans.

Fight Picks

Fight Kuhl’s Pick Petela’s Pick
Main Card (ESPN+, 8 a.m. ET)
WW: Demian Maia vs. Ben Askren Askren Askren
LW: Michael Johnson vs. Stevie Ray Johnson Ray
LW: Beneil Dariush vs. Frank Camacho Dariush Dariush
HW: Ciryl Gane vs. Dontale Mayes Gane Gane
WW: Muslim Salikhov vs. Laureano Staropoli Salikhov Salikhov
Preliminary Card (ESPN+, 5 a.m. ET)
Women’s StrawW: Randa Markos vs. Ashley Yoder Markos Yoder
LW: Rafael Fiziev vs. Alex White Fiziev Fiziev
FW: Enrique Barzola vs. Movsar Evloev Evloev Evloev
HW: Sergey Pavlovich vs. Maurice Greene Pavlovich Greene
Women’s StrawW: Aleksandra Albu vs. Loma Lookboonme Albu Albu
HW: Raphael Pessoa vs. Jeff Hughes Hughes Hughes