Last Updated Aug 30, 2021, 9:58 AM

UFC 239 - Best Bets

The Octagon returns to T-Mobile Center in Las Vegas for Saturday night’s 11-fight UFC 239 card. The show features a pair of title fights, with MMA’s best-ever fighters on the men’s and women’s side defending their respective belts.

Jon ‘Bones’ Jones is set to take on Thiago Santos in the main event. Jones was a -600 favorite at most books as of Tuesday, but the Westgate SuperBook had Jones at -850 late Friday afternoon. Santos was a +575 underdog at the Westgate. Quite a few global shops had Jones at a cheaper price in the -650 neighborhood. The total was 2.5 rounds (‘under’ -135, ‘over’ +105) at most spots.

Jones (24-1-1 MMA, 18-1-1 UFC) has had his hand raised 25 times in 26 career fights. His only “loss” was a disqualification for illegal 12-to-6 elbows in a blowout win over Matt Hamill on Dec. 5 of 2009. His third-round knockout win over Daniel Cormier at UFC 214 was overturned and changed to a no-decision when Jones tested positive for the PED turinabol.

Jones appears – for now at least – to be on the right track outside of the cage recently. This will be his third fight in a span of six months and one week, marking his most activity since 2011-12. He’s indicated he wants to fight at least three times in 2019.

Jones is off a unanimous-decision win over Anthony Smith at UFC 235 in March. He dominated Alexander Gustafsson with a third-round KO victory at UFC 232 on Dec. 29 of 2018. Before those two victories, various suspensions and arrests allowed him to compete just four times in a span of more than five years.

Jones has cleaned out the light-heavyweight division during his dominant career. In a five-fight stretch from March 19 of 2011 to Sept. 22 of 2012, he won the belt and successfully defended it four times. All five of those wins came over former champions – Shogun Rua, Rampage Jackson, Lyoto Machida, Rashad Evans and Vitor Belfort. Only Evans went the distance with Jones during that span.

Santos (21-6 MMA, 13-5 UFC) is 8-1 in his past nine fights since February of 2017. He’s bagged six fight-night bonuses during this stretch. The 35-year-old Santos competed at middleweight his entire career until moving up to 205 pounds to face Eryk Anders in the UFC Fight Night 137 headliner in Sao Paulo last September.

Anders took the fight on six days of notice when Jimi Manuwa pulled out his bout with Santos due to an injury. The former University of Alabama football player had to fly to Brazil and make weight in quick order. Plus, he was going up a weight class for the first time in his career.

The scrap was a slugfest that earned Fight of the Night honors. Unfortunately, Anders collapsed due to exhaustion while trying to walk back to his corner when the third round ended. The referee immediately called the fight to give Santos a TKO victory.

Next, Santos defeated Manuwa with a one-punch KO early in the second round at UFC 231. Then on Feb. 23, he took out Jan Blachowicz with a third-round KO. Santos bagged Performance of the Night bonuses in both wins.

Santos’s only loss since 2017 was a first-round KO defeat against David Branch. His other career losses have come against Vicente Luque, Cesar Ferreira, Uriah Hall, Gegard Mousasi (at UFC 200) and Eric Spicely.

Santos owns other notable career wins over Anthony Smith, Jack Hermansson, Jack Marshman, Nate Marquardt, Elias Theodorou and Steve Bosse.

Prediction: Jones has an outrageous reach advantage yet again in this spot. His 84.5-inch reach is 8.5 inches longer than Santos’s 76-inch reach. Jones is entirely too expensive to bet the straight price and he won’t help you much in a parlay, either. Even the price on Jones to win inside the distance (-195 at most shops) is too rich for me. However, I feel like there’s a good chance that Jones wins by KO/TKO. Let’s go with 1.5 units on Jones to win by KO/TKO for a +185 payout.

In the co-main event, Amanda “The Lioness” Nunes (17-4 MMA, 10-1 UFC) will take on the last legend of women’s MMA, Holly Holm, who isn’t listed on her resume as one of her victims. She’s taken out all the rest – Valentina Shevchenko (twice, albeit in narrow decisions that went the distance), Ronda Rousey, Miesha Tate and Cris Cyborg.

Nunes just became the first women’s double champ by going up to featherweight and handing Cyborg her first loss in more than a decade. Not only did Nunes take her 145-pound strap, but she did it with authority, dusting Cyborg in merely 51 seconds by first-round KO.

Nunes drops back down to bantamweight in this spot to face Holm, who won the women’s bantamweight championship with a second-round KO of Rousey (head kick) back at UFC 193 in Melbourne, Australia.

As of late Friday afternoon, most books had Nunes listed as a -425 favorite with Holm as a +325 underdog. The total was 4.5 rounds (‘under’ -140, ‘over’ +110).

Nunes has won eight consecutive fights and hasn’t tasted defeat since losing to Cat Zingano by third-round TKO (elbows and punches) at UFC 178 on Sept. 27 of 2014. She has six finishes during her eight-fight winning streak, with Shevchenko being the only one that’s gone the distance with her.

Holm (12-4 MMA, 5-4 UFC) has shocked the world before, so it would be foolish to discount her chances of pulling another stunner. After the 37-year-old won the belt from Rousey back in 2015, she made her first title defense against Tate at UFC 196. Holm went to Round 5 with a 3-1 advantage on’s scorecard, but Tate was able to get a takedown. ‘Cupcake’ was eventually able to lock in a rear-naked choke with 90 seconds left in the bout.

Holm dropped a UD to Shevchenko in the five-round headliner of UFC Chicago in the summer of 2016. She then lost a third straight fight by a narrow UD to Germaine de Randamie for the inaugural UFC women’s featherweight belt at UFC 208.

Holm went back to bantamweight and scored a third-round KO win over Bethe Correia at UFC Singapore, bagging an extra 50 large with a Performance of the Night bonus. Next, Holm went back up to featherweight to take on Cyborg for the 145-pound strap. Cyborg won by UD (48-47, 49-46, 48-47) in the UFC 219 headliner. ‘The Preacher’s Daughter’ got back into the win column her last time out, winning a UD over Megan Anderson at UFC 225 in June of 2018.

Prediction: I have tons of respect for Holm and we should certainly note that Tate is the only fighter who has finished her. Nevertheless, it’s hard to pass on prop options for Nunes at plus money. Let’s go with Nunes for one unit to win inside the distance (-105 price) and one unit on her to win via KO/TKO for a +180 return.

Ben Askren (19-0-1 MMA, 1-0 UFC) is set to make his second Octagon appearance against veteran Jorge Masvidal. There’s plenty of bad blood for this one and lots to be learned. There’s a belief that with a victory in this spot, Askren will jump ahead of Colby Covington and get the next shot at Kamaru Usman’s welterweight strap when the champ gets healthy and ready to defend late in 2019.

Askren won his UFC debut by submitting Robbie Lawler late in the first round with a bulldog choke. However, the win was engulfed in controversy, as Lawler never tapped and instantly complained about the stoppage. It’s debatable whether Lawler was out when referee Herb Dean intervened, and ‘Ruthless’ really took it to ‘Funky’ after slamming him on his head in the opening minute of the fight.

Somehow Askren survived a barrage of punches and elbows from Lawler that opened a cut on the face of the former Bellator and ONE Championship’s welterweight kingpin. Askren not only survived, but eventually got back to his feet and was able to work his way toward the submission.

Masvidal (33-13 MMA, 10-6 UFC) has one of the more unique stories in all of MMA. The dude grew up fighting on the streets of Miami – literally. He often took on much bigger men in backyards like the one where Kimbo Slice often hosted bareknuckle scraps.

Masvidal has never been finished in 16 UFC fights and only three times in 46 pro fights. The last time Masvidal was finished was more than a decade ago when Toby Imada submitted him with an inverted triangle choke at Bellator 5 in a lightweight contest.

‘Gamebred’ has dropped four of his six UFC defeats by split decisions, including losses to Al Iaquinta (in the “are you f’n boo-ing me?!” fight in Raging’s Long Island accent), Benson Henderson, Lorenz Larkin and Demian Maia. Masvidal is off a road underdog win in highlight-reel fashion at UFC London, where he dusted Darren Till with a one-punch, left-hook KO from hell in the second round of the main event. He earned Performance of the Night and Fight of the Night bonuses, and then bloodied up welterweight contender Leon Edwards’s face when Edwards started talking trash to Masvidal during a live interview on ESPN+.

As of Thursday, most books had Askren installed as a -220 favorite with Masvidal at +180 on the comeback. The total was 2.5 rounds (‘over’ -220, ‘under’ +175).

Masvidal’s most notable career victories have come over Joe Lauzon, Yves Edwards, KJ Noons, Michael Chiesa, Tim Means, James Krause, Ross Pearson, Jake Ellenberger, Donald Cerrone and Till.

Prediction: Askren’s wrestling is on another level. He was a two-time NCAA champion at the University of Missouri and represented the United States in freestyle wrestling at the 2008 Summer Olympics. Askren is also undefeated in MMA. However, he’ll be outclassed when the fight is standing. Therefore, the obvious question is whether Masvidal can keep the fight standing or not. He did a helluva job in his fight with Maia, defending all submission attempts by perhaps the best there is in Maia. I bet Maia that night and was extremely anxious listening to the judges’ scores. Masvidal’s demeanor during fight week has been impressive. He seems calm, cool, collected and extremely hungry to put a beating on Askren. Let’s go with one unit on Masvidal for a +190 payout (William Hill). Also, we like ‘under’ 2.5 rounds for one unit for a +179 return.

Former middleweight champ Luke Rockhold (16-4 MMA, 5-3 UFC) will make his light-heavyweight debut against Jan Blachowicz. As of late Friday afternoon, most books had Rockhold installed as a -240 favorite with Blachowicz as a +190 underdog. The total was 1.5 rounds (‘over’ -160, ‘under’ +140).

Rockhold lost his UFC debut to a juiced-up Vitor Belfort by first-round KO in May of 2013, but he responded with a five-fight winning streak. Rockhold finished Costas Philippou and Tim Boetsch in the opening round. Then he collected back-to-back Performance of the Night bonuses in second-round submission victories over Michael Bisping and Lyoto Machida, setting up a title shot against then-undefeated Chris Weidman.

Rockhold trounced Weidman by fourth-round KO to win the 185-pound strap. He was set to face Weidman in a rematch at UFC 199, but the ‘All-American’ pulled out of the contest due to an injury. Bisping accepted the fight on two weeks of notice and pulled a stunner with a first-round KO victory over Rockhold as a +500 underdog.

Rockhold returned to the Octagon 15 months later and beat David Branch via second-round KO. In his last time out, however, Rockhold lost to Yoel Romero by third-round KO on Feb. 10 of 2018.

Blachowicz (23-8 MMA, 6-5 UFC) had his four-fight winning streak snapped on Feb. 23 when Thiago Santos beat him via third-round KO. The 36-year-old Polish fighter will have a one-inch reach advantage on Rockhold (77 inches).

Prediction: I think Rockhold wins but I don’t trust him enough to lay the expensive price. I’ll pass.

In the opener of the main card, Michael Chiesa and Diego Sanchez will square off in a welterweight contest. As of late Friday afternoon, most spots had Chiesa (15-4 MMA, 8-4 UFC) listed as a -360 ‘chalk’ with Sanchez at +280 on the comeback. The total was 2.5 rounds (‘under’ -130, ‘over’ +100).

The 31-year-old Chiesa won Season 15 of the Ultimate Fighter by submitting Iaquinta in the first round back on June 1 of 2012. He is fighting at 170 pounds for the second time. Chiesa defeated Carlos Condit by second-round submission (one-armed kimura) at UFC 232 in his welterweight debut.

Chiesa owns notable career scalps over Beneil Dariush, Jim Miller, Francisco Trinaldo and Mitch Clarke.

Sanchez (29-11 MMA, 18-11 UFC) is seeking his first three-fight winning streak in more than a decade. On June 20 of 2009, Sanchez captured a split-decision victory over Clay Guida for his fourth consecutive victory. The scrap earned 2009 Fight of the Year honors and set Sanchez up with a title shot against B.J. Penn. Sanchez, who has competed in four different divisions, lost by fifth-round TKO (doctor stoppage) to ‘The Prodigy’ at UFC 107 in Memphis.

The 37-year-old Sanchez just left his hometown camp/team, Jackson-Wink Academy in Albuquerque, about six weeks ago. He’s now working with trainer Joshua Fabia. Sanchez was with Jackson-Wink from 2002-07 and 2010-19.

‘Nightmare’ was the winner of the middleweight tournament in Season 1 of The Ultimate Fighter. Sanchez has been a staple of the promotion for more than 14 years, and he’ll make his 30th career walk to the Octagon on Saturday night.

Sanchez has participated in the Fight of the Night seven different times. His most notable career victories have come over Nick Diaz, Martin Kampmann, Takanori Gomi, Guida, Joe Stevenson, Jorge Santiago, Kenny Florian, Karo Parisyan, Joe Riggs, Paulo Thiago. Guida, Jim Miller and Ross Pearson.

Sanchez fought only once in 2018, winning a UD over Craig White at UFC 228. Then at UFC 235 in March, he trounced Mickey Gall via second-round KO (punches) to earn a Performance of the Night bonus.

Prediction: Chiesa has 11 career submission victories, but Sanchez has never been submitted. He has seven submission wins of his own. I thought Sanchez’s career was over after Matt Brown beat him with a monster elbow on Nov. 11 of 2017. However, I like what I’ve seen out of Sanchez lately and it seems like a good matchup for him. Chiesa is the younger fighter that has better quickness and speed, but those advantages are negated a bit when the fight goes to the ground. I give Sanchez a decent shot here. Let’s go with one-half unit on Sanchez for a +315 payout.

In the prelims headliner on ESPN, Gilbert Melendez (22-7 MMA, 1-5 UFC) takes on Arnold Allen. As of Friday, most books had Allen installed as a -360 ‘chalk’ with Melendez as a +280 underdog. The total was 2.5 rounds (‘over’ -280, ‘under’ +230).

‘El Nino,’ the former Strikeforce lightweight champion, is fighting for the first time since losing a lopsided decision (30-26, 30-25, 30-26) loss to Jeremy Stephens at UFC 215 on Sept. 9 of 2017. Melendez hasn’t won since beating Sanchez via UD in an Instant Classic at UFC 166 on Oct. 19 of 2013. He’s limped to a 1-5 record since joining the promotion, but we should note that he’s faced three former UFC lightweight champions.

Two of those losses – to Benson Henderson and Eddie Alvarez at UFC 188 – came by split decision. Melendez has notable career victories over the likes of Guida, Josh Thomson (twice), Masvidal, Rodrigo Damm, Sanchez and Shinya Aoki.

Allen (14-1 MMA, 5-0 UFC) is a 25-year-old Brit who is off a UD victory over Jordan Rinaldi. He’s collected a pair of Performance of the Night bonuses during his five-fight UFC tenure, with submission wins over Alan Omer (guillotine choke) and Mads Burnell (front choke).

The rest of the prelims look like this: Marlon Vera (-400) vs. Nohelin Hernandez (+320), Claudia Gadelha (-250) vs. Randa Markos (+200) and Yadong Song (-220) vs. Alejandro Perez (+170).

The Early Prelims will be aired on UFC Fight Pass starting at 6:30 p.m. Eastern.

B.E.’s Octagon Nuggets

-- Paul Felder will face Edson Barboza in a rematch between lightweight contenders at UFC 242. Barboza won the first meeting in the summer of 2015 in a contest that garnered Fight of the Night honors. Barboza is on a 1-3 slide in his past four outings, while Felder is off a UD win over James Vick.

-- Cerrone told MMAJunkie Radio this week that he’s begging for a rematch with Tony Ferguson. Cerrone said, “August, hopefully no later than September. I can’t fight any later than September, because now I’m running into not being able to get two more at the end of the year.” Cerrone also claimed that Conor McGregor has turned down fights against him multiple times. “[Conor’s] turned me down three or four times now. We were supposed to do it, and it just deteriorated. I don’t know, he just won’t sign his end of the deal.”

-- Robert Whittaker vs. Israel ‘The Last Stylebender’ Adesanya to unify the welterweight championship is official for UFC 243, but the venue hasn’t yet been finalized. The show is expected to take place in Australia.

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