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UFC 244: Masvidal vs Diaz - Odds and Predictions

Written by: Ryan Bristlon
Updated October 14, 2022
11 min read

How to Watch UFC 244

Where: Madison Square Garden – New York, NY.

When: Saturday, November 2, 10 PM EST

How (TV): UFC Fight Pass, ESPN+, pay-per-view

UFC 244

UFC 244 will be the organization’s 500th live event since the companies inception in 1993.

One may expect this to mean that the card would be stacked with several title and title-contender fights, but that is not the case.

UFC 244 is a first pay-per-view card in years to not have a single title fight on the bill. However, that hasn’t stopped the UFC from putting together one of the most talent-heavy cards in recent memory – from the main event all the way to the prelims.

The main event between Nate Diaz and Jorge Masvidal was almost lost due to Diaz having a, well, strange drug test result. But his name has since been cleared and barring no late injuries or weight cutting issues, the UFC 244 card is set to go off as follows:

Jorge Masvidal vs Nate Diaz – Welterweight Division

Sportsbook Masvidal Diaz
bet365 NJ -170 +140
DraftKings -182 +147

Ok, so we guess there is a title fight on the card after all.

Nate Diaz and Jorge Masvidal will be fighting for the title of the UFC’s BMF: baddest mother (expletive).

UFC president Dana White has gone as far as constructing a one-time specialty championship belt to award to the fight’s winner.

As mentioned earlier, the fight was almost scrapped last week after Diaz tested for abnormally high amounts of a banned substance. It was quickly proven that the substance was from a contaminated daily vitamin and Diaz was given the green light to participate in the fight this Saturday.

Jorge Masvidal (34-13)

Jorge Masvidal, 34, is riding a wave of success.

After dropping back-to-back losses in 2017 against Stephen Thompson and Demian Maia, Masvidal went through all of 2018 without a fight. Since returning to the octagon in 2019, Masvidal has been a force to be reckoned with.

Back in March, Masvidal fought Darren Till in Till’s home country of England.

Masvidal knocked out Till with a brutal punch that left Till unconscious for several minutes after the fight.

In his most recent fight, Masvidal shook the MMA world to its core when he handed undefeated fighter Ben Askren the first loss of his career with a flying knee knockout in the first round that now registers as the UFC’s fastest knockout in history: five seconds.

”Gamebred” stands at 5 feet, 11 inches tall and has a reach of 74 inches. The former lightweight fights out of Florida with the American Top Team gym.

Known for his kickboxing style, Masvidal has also spent time training with the Phuket Top Team gym. Previously fighting under the Strikeforce and Bellator banners, Masvidal is now currently ranked as the number-three welterweight in the UFC.

Nate Diaz (20-11)

Nate Diaz, 34, is fighting for his second time in 2019. Prior to his last fight, Diaz had not fought since the summer of 2016 when he lost his rematch with Connor McGregor via unanimous decision.

Diaz returned to the octagon on August 17 at UFC 241 where he took on Anthony Pettis who had recently moved up to the welterweight division.

Ring rust appeared to be non-existent and Diaz put on a stellar performance that saw him take a unanimous judges’ decision.

Nate Diaz stands at an even 6 feet tall and has a reach of 76 inches. He will have a two-inch reach advantage over Masvidal.

Diaz entered the UFC after winning the Ultimate Fighter season five and has fought at both lightweight and welterweight. Known for his submission and boxing skills, the southpaw fighter trains out of Stockton, California at the Cesar Gracie academy.

Under coach Cesar Gracie, Nate Diaz has a second-degree black belt in Brazilian jiu-jitsu. He has been active in MMA since 2004 and is currently ranked as the sixth-best welterweight by the UFC.

Kelvin Gastelum vs Darren Till – Middleweight Division

Sportsbook Gastelum Till
bet365 NJ -188 +162
DraftKings -177 +135

Kelvin Gastelum (15-4-1)

Kelvin Gastelum, 27, is looking to bounce back after losing his interim title fight against Israel Adesanya earlier this year in what was truly a fight of the year contender.

Prior to his unanimous decision loss to Adesanya back on April 13 at UFC 236, Gastelum had put together an impressive two-fight winning streak.

In 2017, Gastelum knocked out the former middleweight champion Michael Bisping in what would turn out to be Bisping’s last professional fight. Gastelum followed that win with a split-decision victory over the always dangerous “Jacare” Souza in 2018.

Kelvin Gastelum, an American-born fighter, stands at 5 feet, 9 inches tall and possesses a reach of 71.5 inches long.

Training out of Arizona, Gastelum trains his boxing and jiu-jitsu with Kings MMA. He has a black belt in 10th Planet jiu-jitsu under Brian Beaumont.

He is a southpaw fighter who has been active in mixed martial arts since 2010.

The winner of the Ultimate Fighter season 17, Gastelum is currently ranked as the fourth-best middleweight in the division.

Darren Till (17-2-1)

Darren Till, 26, entered the UFC with an undefeated record and won his first five fights straight in the UFC with one draw.

The win streak included wins over notable fighters such as Stephen Thompson and Donald Cerrone.

This streak led to Till being granted a title shot against then-champion Tyron Woodley.

Woodley handed Till the first loss of his career as Till tapped out to a d’arce choke in the second round.

Till’s most recent fight, which took place earlier this year, saw him go toe-to-toe with Jorge Masvidal.

As mentioned earlier, Masvidal knocked Till out in the second round of their bout.

After losing two fights in a row, Till will now make the jump to the middleweight division and jumps right into the mix against one of the division’s best.

Born in Liverpool, England, “The Gorilla” stands at an even 6 feet tall.

He has a 74.5-inch reach which will give him a three-inch reach advantage over Gastelum this Saturday night. Like his opponent, Till is a southpaw, but unlike Gastelum, he is known for his muay thai and luta livre skills.

Fighting out of Liverpool, Till trains with Team Kaobon in England and the Astra Fight team in Brazil.

He has been active in MMA since 2013 and has a purple belt in luta livre. He is currently unranked in the middleweight division but still ranks at number-nine in the welterweight rankings.

Stephen Thompson vs Vicente Luque – Welterweight Division

Sportsbook Thompson Luque
bet365 NJ -125 +100
DraftKings -141 +110

Stephen Thompson (14-4-1)

Stephen Thompson, 36, has been struggling in his UFC career as of late.

Thompson joined the UFC in 2012 and went 8-1 in his first nine UFC fights. He then received a title shot against then-champion Tyron Woodley in 2016 but the fight was declared a draw.

A rematch was set that Thompson would lose via majority decision. Since the Woodley fights, Thompson has gone just 1-2.

He bounced back from the Woodley loss to defeat Jorge Masvidal in 2017 at UFC 217 but then lost two in a row. One against Darren Till by unanimous decision and one via knock out against Anthony Pettis earlier this year in March.

”Wonderboy” stands at 6 feet tall and has a reach that measures 75 inches.

Fighting out of South Carolina, Thompson trains with both the Pitch Black MMA and the Serra-Longo Fight Team with trainers Ray Thompson and Carlos Machado.

Thompson is a fighter with top-notch credentials including a fifth-degree black belt in Kempo karate, a black belt in jujutsu, a black belt in American kickboxing, and a brown belt in Brazilian jiu-jitsu under Carlos Machado.

He has an undefeated 58-0 professional kickboxing record and has been active in MMA since 2010. He is currently ranked as the eighth-best welterweight in the UFC.

Vicente Luque (17-6-1)

Vicente Luque, 27, has become quite the break out star in the UFC’s welterweight division.

Since joining the UFC, Luque has put together a record of 10-1 with his lone loss under the banner being against Leon Edwards by decision.

Currently riding a six-fight winning streak that includes wins over fighters such as Niko Price and Derrick Krantz, it was Luque’s most recent fight that really made the headlines for the young fighter.

On August 10, Luque defeated Mike Perry via split-decision and he left Perry with a nose so broken that he was hardly recognizable after the fight.

He earned his second fight of the night bonus for that performance.

”The Silent Assassin” stands one inch shorter than his opponent at 5 feet, 11 inches.

His reach, however, measures 75.5 inches, giving him an advantage of one-half-inch.

The Brazilian fighter trains in Brazil with Cerrado MMA and Hard Knocks 365.

He currently has a brown belt in Brazilian jiu-jitsu and a purple belt in luta livre. He has been active in mixed martial arts since 2009 and currently sits just inside the top-15 welterweight rankings at number 14.

Derrick Lewis vs Blagoy Ivanov – Heavyweight Division

Sportsbook Lewis Ivanov
bet365 NJ +100 -125
DraftKings -106 -121

Derrick Lewis (21-7-1)

Derrick Lewis, 34, is one of the most decorated UFC heavyweights when it comes to fight bonuses.

Lewis has six post-fight bonuses since 2016. After riding a three-fight winning streak, Lewis lost his only title shot to date against former champion Daniel Cormier where he was submitted in the second round. Lewis’ last fight came against Junior dos Santos earlier this year on March 9.

Although Lewis received fight of the night honors, it was dos Santos who came out victorious over Lewis with a TKO victory.

It was the first time in Lewis’ career that he has lost two fights in a row.

”The Black Beast” stands at 6 feet, 3 inches tall and has a reach of 79 inches.

Fighting out of Texas, the American-born fighter trains under coach Bob Perez at the 4oz Fight Club gym. Known predominantly for his boxing and his knock out power, Lewis has been active in MMA since 2010. He is currently ranked as the UFC’s fifth-best heavyweight in the division.

Blagoy Ivanov (18-2-1)

Blagoy Ivanov, 33, is currently riding a two-fight win streak since dropping his UFC debut against Junior dos Santos.

Ivanov bounced back from the dos Santos loss with a unanimous decision victory over Ben Rothwell in March.

He went on to fight once again this year on June 8 against Tai Tuivasa at UFC 238. Ivanov defeated Tuivasa by unanimous decision.

”Bagata” is a Bulgarian-born fighter who stands four inches shorter than his opponent at 5 feet, 11 inches.

He has a reach of 73 inches – six inches shorter than Derrick Lewis.

A sambo specialist, Ivanov trains in his home country at Combat Sambo and at the American Kickboxing Academy when States-side.

He has an international master of sports in sambo and a black belt in judo, a discipline in which he almost competed in the Olympics for.

He has been active in MMA since 2007 and is ranked as the UFC’s number-eight heavyweight.

Kevin Lee vs Gregor Gillespie – Lightweight Division

Sportsbook Lee Gillespie
bet365 NJ +137 -163
DraftKings +130 -167

Kevin Lee (17-5)

Kevin Lee, 27, is returning to the lightweight division after dropping his last fight in which he moved up a weight class to welterweight.

In that last fight which took place on May 18, Lee fought Rafael dos Anjos (another former lightweight) and lost via fourth-round arm-triangle choke submission.

Prior to that fight, Lee lost a unanimous decision to Al Iaquinta late last year.

Kevin Lee has gone just 2-3 in his last five fights and currently has two losses in a row.

”The Motown Phenom” is an American-born fighter that stands at 5 feet, 9 inches tall.

He has a reach of 77 inches and fights with an orthodox stance.

Fighting out of Las Vegas, Lee recently moved his training to the Tristar gym in Montreal, Canada, the gym famous for training UFC great Georges St. Pierre. Active in MMA since 2012, Lee possesses NCAA division II wrestling credentials and is currently ranked as the tenth-best lightweight in the division.

Gregor Gillespie (13-0)

Gregor Gillespie, 32, is not only undefeated in the UFC, but he is also undefeated throughout his entire MMA career.

The wrestling prodigy has won six-straight in the UFC with his most recent win coming on January 19.

He fought and defeated Yancy Medeiros via TKO in the second row.

His last five fights have all been won by submission, KO, or TKO and he has three UFC post-fight bonuses to his name.

”The Gift” stands at 5 feet, 7 inches tall, giving him a two-inch height disadvantage heading into his fight the Saturday night.

He will also have a six-inch reach disadvantage as his reach measures at only 71 inches.

The Long Island-born fighter trains in his home city with Long Island MMA. He has NCAA Division I wrestling credentials and has been active in MMA since 2012.

He is currently ranked as number-11 in the UFC lightweight rankings.

Honorable prelim mention

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Corey Anderson vs Johnny Walker – Light Heavyweight Division

Sportsbook Anderson Walker
bet365 NJ +137 -163
DraftKings +130 -167

Headlining the prelims of UFC 244 is a light heavyweight bout between two top contenders who have both left fans in awe with their performances. This bout between Johnny Walker and Corey Anderson could just as easily be found on the main card and this we are going to treat it as such.

Corey Anderson (12-4)

Corey Anderson, 30, has been very vocal about his desire to fight for the light heavyweight title this year after going 3-0 in 2018.

However, Anderson has yet to fight in 2019. Anderson’s three-fight win streak includes wins over Patrick Cummins, Glover Texeira, and Ilir Latifi – all of which were won by unanimous decision.

”Overtime” stands at 6 feet, 3 inches tall and has a reach of 79 inches.

Anderson is an American-born fighter who fights out of Illinois.

He trains with the Ricardo Almeida BJJ academy and has a purple belt in Brazilian jiu-jitsu under Almeida himself.

Known for his wrestling and boxing, Anderson has NCAA division III wrestling credentials. He has been fighting professionally since 2013 and is currently ranked as the UFC’s number-seven light heavyweight.

Jonny Walker (17-3)

Johnny Walker, 27, is undefeated thus far in the UFC.

In fact, Walker has yet to have a fight enter its second minute.

All three of Walker’s UFC fights have ended in the first round and earned him performance of the night bonuses.

Walker’s most recent fight came on March 2 against Misha Cirkunov. Walker won via TKO after landing a flying knee. However, Walker hasn’t fought since due to injuring his shoulder in his post-fight celebration.

The Brazilian-born fighter comes into this fight with most of the physical advantages.

Walker stands two-inches taller than Anderson at 6 feet, 5 inches tall.

He also has a reach of 82 inches, giving him a three-inch reach advantage Saturday night.

Walker trains in both Dundee and Thailand and is affiliated with the Imperio Fight Team. He has been active in MMA since 2013 and has a brown belt in Brazilian jiu-jitsu. He is currently ranked as the 11th-best light heavyweight in the UFC.

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Ryan Bristlon

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Ryan Bristlon is a Canadian writer currently residing in Hamilton, Ontario. He studied print and broadcast journalism at Humber College and has been a lifelong fan of the sport of hockey and the NHL.

Email: [email protected]

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