MMA Junkie analyst Dan Tom breaks down the UFC’s top bouts. Today, we look at the main event for UFC on ESPN+ 20.
UFC on ESPN+ 20 takes place Saturday at Singapore Indoor Stadium in Singapore. The card streams on ESPN+.
Demian Maia (27-9 MMA, 21-9 UFC)

Staple info:
- Height: 6’1″ Age: 41 Weight: 170 lbs. Reach: 72″
- Last fight: Decision win over Anthony Rocco Martin (June 29, 2019)
- Camp: Demian Maia Jiu-jitsu (Brazil)
- Stance/striking style: Southpaw/kickboxing
- Risk management: Good
Supplemental info:
+ Brazilian jiu-jitsu black belt
+ 2x Brazilian jiu-jitsu champion
+ 2007 ADCC winner
+ 3 KO victories
+ 13 submission wins
+ 11 first-round finishes
+ 21-2 with at least 1 takedown secured
+ Improved striking
^ Underrated left hand
+ Excellent wrestling ability
^ Solid hips, under-hooks, takedowns
+ Superb top game
^ 94 passes in 29 fights
+ Steady and smooth transitions
^ Always looks for the back
Ben Askren (19-1 MMA, 1-1 UFC)

Staple info:
- Height: 5’11” Age: 35 Weight: 170 lbs. Reach: 72″
- Last fight: Knockout loss to Jorge Masvidal(July 6, 2019)
- Camp: Roufusport (Milwaukee)
- Stance/striking style: Orthodox/kickboxing
- Risk management: Good
Supplemental info:
+ Bellator and ONE Championship welterweight titles
+ 2x NCAA Div. 1 national champ
+ 4x NCAA Div. 1 All-American wrestler
+ 6 KO victories
+ 6 submission wins
+ 10 first-round finishes
+ Relentless pace and pressure
^ Deceptive athleticism
+/- Developing striking game
^ Primarily uses it to make entries
+ Strong inside the clinch
^ Superb from body lock position
+ Chains together takedowns well
+ Excellent transitional grappler
^ Rides and scrambles seamlessly
Point of interest: Striking?
The main event in Singapore features an interesting matchup between two grappling specialists who could find themselves spending more time fighting on the feet than they’re used to.
A decorated grappler both in and out of the gi, Demian Maia stepped onto the MMA scene as a fighter who was still learning how to strike while on the job.
Operating out of his patented southpaw stance, we have seen a few different iterations of Maia’s striking over the years. From his kick-heavy approach under Wanderlei Silva’s wing to his more boxing-centric tactics since working with Luiz Doria (Junior Dos Santos’ boxing coach), Maia is more than competent at throwing all four of his limbs.
Sure, his initial foray of striking with high-level opposition wasn’t exactly his best stretch at middleweight (otherwise known as Maia’s “K-1 era” to hardcores), but that provided a useful experience for the Brazilian to work through any discomfort or unknowns in his game. And regardless of what weight Maia was operating at, he has always wielded a deceptively heavy left cross that Ben Askren will need to be aware of.
Askren, who made his name in the wrestling world by becoming one of two men to earn the Dan Hodge Trophy twice (amidst many other accolades), is no stranger to having an on-paper disadvantage when striking on the feet.
The former Mizzou Tiger makes no qualms about using his striking as more of a means to an end – though one has to wonder if Askren’s attitude has changed since his last fight.
In Askren’s defense, he’s shown an ability to absorb big shots and damage throughout his career, but – perfect flying knee or not – you cannot rely too heavily on your chin at the upper echelons of MMA. Thankfully for Askren, he seemed to have taken the knockout loss to Jorge Masvidal well (all things considered), not appearing to let it affect his near-unshakable confidence.
That said, Askren’s confidence, at least for me, will be the thing worth watching for in this fight.
Askren arguably lets his confidence fuel him on the feet, showing little issue when having to stalk forward into turbulent territory, occasionally throwing spinning attacks when feeling in stride. Still, with wrestling being Askren’s ultimate goal in mind, fighters who can offer up something in the counter-wrestling department have typically been the American standout’s toughest tests.
Next point of interest: Wrestling vs. presenting
Point of interest: Wrestling vs. presenting

With the wrestling advantages obviously going to Askren on paper, many wonder how the All-American national champ will conduct business opposite a crafty submission specialist who presents opportunities in order to gain ground.
After a failed bid for the UFC middleweight throne, Maia eventually embraced both wrestling and weight-cutting, dropping down to the welterweight division in 2012.
Storming the ranks at 170 pounds with first-round finishes over Dong Hyun Kim and Rick Story, Maia fell in love with a wrestling style that melded his MMA and jiu-jitsu games into one solid sword of offense.
Deceptively strong inside the clinch, Maia demonstrates excellent use of underhooks and a preternatural ability to keep his hips in close to his opposition. From this area of the fight, Maia’s background in judo and karate shine through in the way in which he utilizes slick trips and sweeps to finish takedowns.
But the question remains: Will Maia be able to get Askren down?
We know that Askren’s offensive wrestling abilities are well intact, but we’ve seldom ever seen him have to meaningfully counter wrestle in MMA for extended periods of time. In fact, the only high-level submission artist that Askren faced was a smaller Shinya Aoki, who pulled guard early before being stopped with strikes from the full-guard soon after.
That said, it’s still hard to doubt the defense of a two-time NCAA national champion who finished his collegiate wrestling career on an 87-match win streak (all dominant victories that saw the scoring margins widen, not narrow). In other words: Askren can not only take the lead, but he can protect it as well.
Nevertheless, do not be surprised if Askren incorporates consistent offense here.
The former Mizzou Tiger can hit things like level-changing doubles to get things done, but does his best work when getting in on a body lock. Once able to clasp his hands, Askren hits persuasive trips or tosses that he can chain from one to another if he chooses to. And given the submission threat at hand, clinch takedowns may be among his safer avenues to get offensive.
However, I can’t help but wonder how Askren’s funky stylings will stack up in this matchup – especially if he gets too confident or careless with his approach.
As the nickname “Funky” would suggest, Askren developed his brand of funk-style out of necessity to stay afloat with what he felt were more athletic wrestlers, utilizing things like scrambles and his deep index of wrestling leverage to come out on top. Even then, you could see his natural aptitude for grappling as Askren was already utilizing positions like 50-50 leg entanglements to reverse or steer opposition, sometimes earning pins out of his efforts.
In MMA, Askren obviously has been a bit more judicious with his approach given the strikes and submissions at play. However, this has not necessarily been good news for any of Askren’s opponents considering the relentless wave of strikes from wrist-ride positions that are likely coming their way.
But as technically sound as Askren is, he will need to be mindful of Maia’s tricks.
Fitting a fighter archetype that I like to classify as a “presenter,” Maia will present a positional situation or opening as bait to gain ground in the bigger picture.
Against Matt Brown, for example, Maia demonstrated his presenting abilities by selling a scene of vulnerability off of failed takedowns – when his ultimate objective was to establish contact by pulling to half guard (a tactic that fellow Brazilian jiu-jitsu black belt Antonio Rodrigo Nogueira wrote the book on during his days in PRIDE). And though Maia will typically eat a shot or two for his troubles, he inevitably finds a home for his half-guard-to-single-leg transition, sucking his opposition into his brand of quicksand and tricking them into grappling space.
If Maia can get his American counterpart to play his style of chess, then perhaps we will get some fun exchanges that give us an even better idea of Askren’s MMA capabilities.
Next point of interest: Odds, opinion and prediction
Point of interest: Odds and opinions

The oddsmakers and public seem to be siding with the American, listing Askren -185 and Maia +160 as of this writing.
Though this is admittedly not a confident pick for me, I can’t help but agree with the betting line above. In fact, if recency bias didn’t spotlight Askren being nearly decapitated by a surging Masvidal, then I think we’d see an even wider spread in this matchup.
Don’t get me wrong: Maia has multiple ways to win this fight, whether it be on the feet or on the mat. Not only does Maia have both the positional and submission savvy to check Askren, but he will also be the better striker in this fight by a decent stretch.
Maia carries an accurate and deceptively heavy left hand that I see having play on Askren anytime these two exchange on the feet. The potential problem, however, is that I’m not sure how Maia will become the one who dictates where this fight takes place.
Not only does Askren already have the proper defensive reps from a training camp spent prepping for Maia with teammate Tyron Woodley, but I believe his understanding and unabashed attitude toward submission grappling may be his saving grace here.
From his willingness to jump into ADCC tournaments to his humbleness of publicly putting himself through the wringer with grappling greats like Marcelo Garcia, I suspect that Askren has only continued to sharpen his submission awareness over the years. He also religiously fights hands (both defensively and offensively) – a tactic that I consistently preach as grappling’s “unsung hero.”
Maia is both one of my favorite grapplers and human beings in this sport, so seeing him come out on top here would be gratifying. But even in his prime, Maia’s grappling gas tank has been hit and miss, as I suspect that Askren has the better cardio and healthier hips at this point in their respective careers. Ultimately, I have a hard time not seeing Askren being the one who dictates terms down the stretch of a competitive five-round affair.