UFC 309 betting tips: 4 undercard fights to follow at Madison Square Garden

Simon Head is back to run through the UFC 309 undercard in the Big Apple.

UFC 309 Tips

Charles Oliveira v Michael Chandler – Oliveira by KO/TKO or submission
Bo Nickal v Paul Craig – Nickal by KO/TKO
Chris Weidman v Eryk Anders – Fight to go the distance
Jim Miller v Damon Jackson – Miller by decision

*All prices are bang up to date with our snazzy widgets, while odds in copy are accurate at time of publishing but subject to change.

UFC 309
Madison Square Garden, New York
TV: TNT Sports Box Office
Overnight Saturday November 16th-Sunday November 17th

The iconic Madison Square Garden in New York City will play host to one of the biggest UFC pay-per-view cards of 2024 as UFC 309 pits two bona-fide legends of the game head to head in a titanic heavyweight championship main event.

Former light heavyweight champion and current undisputed heavyweight king Jon “Bones” Jones will put his title on the line against the UFC’s greatest-ever heavyweight champion, Stipe Miocic, in a battle of two of the Octagon’s all-time greats.

But, before the heavyweight title tussle in the headline bout, there’s a packed card of fights leading up to the main event. I’ve picked out four crucial clashes to keep your eye on, and shared a pick for each one.

Charles Oliveira v Michael Chandler

Sunday 4:45am

Two of the most exciting lightweights on the planet will go to war for a second time as former UFC lightweight champion Charles Oliveira and former three-time Bellator lightweight champion Michael Chandler do battle in a huge clash at 155 pounds.

It’s a matchup that both men hope will push them to the front of the line to challenge reigning lightweight champ Islam Makhachev in 2025, and a fight that both men will be confident of winning.

That’s because, despite Oliveira’s second-round TKO finish of Chandler in their first meeting back at UFC 262 in May 2021, the fight very nearly didn’t even make it to Round 2. Chandler absolutely battered “Do Bronx” at the end of the first round in Houston that night, and only the buzzer stopped him from claiming a first-round finish of his own.

But Oliveira survived the round, used the break between rounds to recover, and stunned Chandler in the opening seconds of Round 2 to claim an incredible finish just 19 seconds after the restart. Now both men want to run it back, and both want to get a big win to earn a shot at Makhachev early next year.

Oliveira undoubtedly has more weapons at his disposal, the former champion is the UFC’s all time leader in finishes (20), submissions (16) and post-fight bonuses (19), which means he’s must-see TV whenever he steps into the Octagon. It also makes him one of the most dangerous fighters to share the cage with.

But Chandler has never been one to shy away from a challenge and, despite a record that looks spotty on paper, the American always brings the action, and is always competitive in his fights, even the ones he loses. His wrestling prowess allows him to keep the fight on the feet, where he uses his heavy hands to give his opponents problems. Arguably, he should use that wrestling background more to get takedowns and dominate on the mat, but typically that hasn’t been his style, with Chandler presenting himself as an out-and-out crowd pleaser.

It means the rematch is likely to be every bit as wild as their first meeting. And, in a wild fight, I’ll side with the fighter with more ways to win. Oliveira has the skills to get the job done on the feet or on the mat. He did it inside the distance in their first meeting, and he’s the smart pick to repeat the feat again on November 16. Oliveira by KO/TKO or Submission is the play.

Bo Nickal v Paul Craig

Sunday 4:15am

Former college wrestling phenom Bo Nickal has been perfect inside the Octagon in his three UFC fights so far, but already some fans are getting frustrated that he hasn’t faced tougher competition on the sport’s biggest stage.

That all changes on November 16 when Nickal takes on former light heavyweight contender and dangerous submission specialist Paul Craig at UFC 309. It’s the toughest test of Nickal’s UFC career to date, but will he pass it?

In a sport where so many different skills and disciplines are in play, Craig is as close to a specialist as you’ll find. He can certainly strike, but his bread and butter is his jiu-jitsu. The Scot has claimed 13 of his 17 career victories via submission, including the scalp of the division’s current top contender, Magomed Ankalaev, who he subbed in the final second of their bout at UFC London back in 2018. He also snapped future champion Jamahal Hill’s arm in a TKO victory in 2021.

But, while Craig has repeatedly shown the ability to pull a submission out of nowhere, he has shown his Achilles heel to be his striking. Despite a decent jab, his striking hasn’t been able to deter the top-level contenders, and losses to Volkan Oezdemir, Johnny Walker and Caio Borralho showed the blueprint for how to defeat “Bearjew.”

The big question going into this one is how Nickal will choose to approach the matchup. If he looks for the clearest, smoothest, quickest path to victory, he’ll keep it standing and look to use his heavy-handed striking to put Craig under pressure and, eventually, land something big.

But Nickal is a proud wrestler, and the former Penn State standout might want to showcase his dominance against a dangerous grappler, just to make a statement to the rest of the division. If he does that, it’ll certainly make more people sit up and take notice, but it will also put him firmly in the danger zone, with Craig one of the most dangerous men in the UFC fighting off his back.

Nickal is a smart operator, and I expect him to stand and strike, and claim a stoppage victory on the feet inside the first two rounds. I’m on Nickal by KO/TKO.

 

Chris Weidman v Eryk Anders

Sunday 2:10am

If you’re booked to fight Eryk Anders, bring your lunch, and make sure your cardio is on point, because the chances are you’re in for a long night.

In 25 career fights, “Ya Boi” has lost just twice inside the distance, with his six other losses coming on the scorecards. He’s a rough, tough, durable middleweight with experience at middleweight and light heavyweight.

It means he’s a tough bout for former middleweight champion Chris Weidman, who could potentially be stepping into the Octagon for the final time as he competes on home soil in New York.

The former undisputed 185-pound champion has endured some horrific injuries since his time as middleweight champ, and it’s a miracle he’s still fighting at this level after shattering his leg against Uriah Hall back in 2021.

Incredibly, Weidman has fought twice since then, losing a decision to Brad Tavares and claiming a technical decision win over Bruno Silva in a controversial fight in Atlantic City back in March.

Weidman looks a shadow of the fighter who captured 185-pound gold by knocking out the great Anderson Silva, and it’s likely that this one could go all the way to the scorecards. Anders will likely close as the narrow betting favourite, but the smart bet here is on the fight to go the distance, rather than siding with a particular fighter.

 

Jim Miller v Damon Jackson

Sunday 1:40am

One of the all-time greats of the Octagon continues his incredible career as Jim Miller returns to action against Damon Jackson at UFC 309.

The fight will be Miller’s 56th career fight, and his 45th bout in the UFC as he extends his record as the man with the most fight appearances in UFC history. And the 41-year-old from New Jersey plans on claiming his 38th victory to an already incredible resume.

Miller has won five of his last seven, and looks as strong as ever, while Jackson has the toughness to hang with him for the full three-round duration. The key difference could be the weight class. Miller is a seasoned lightweight, while Jackson is moving up from featherweight to take the fight.

It’s a great piece of matchmaking by the UFC, and I’m going to lean towards the veteran getting the job done after three hard rounds. Miller by Decision is the pick.

UFC 309 Tips

Charles Oliveira v Michael Chandler – Oliveira by KO/TKO or submission
Bo Nickal v Paul Craig – Nickal by KO/TKO
Chris Weidman v Eryk Anders – Fight to go the distance
Jim Miller v Damon Jackson – Miller by decision

*All prices are bang up to date with our snazzy widgets, while odds in copy are accurate at time of publishing but subject to change.

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