Best Boxing Matches to Bet on in May 2021

| April 28, 2021 9:43 am PDT

There are some huge fights to bet on this May, and I’m going to reel off ten of the very best.

Typically, May is one of the better months for the sport, with the Cinco de Mayo weekend traditionally the pinnacle of pugilistic excellence.

Over the years, Oscar de la Hoya and Floyd Mayweather ran the show in the month of May, but that torch is now in the hands of the one and only Canelo Alvarez.

I’ll be covering Canelo’s fight with Billy Joe Saunders, as well as more of the best boxing matches you can bet on in May 2021.

Let’s go.

Derek Chisora vs. Joseph Parker

  • When: May 1, 2021
  • Where: Manchester Arena – Manchester, England

The first major boxing match to bet on this May is, suitably enough, a heavyweight contest.

Britain’s Derek Chisora (32-10) fights New Zealand’s Joseph Parker (28-2) in Machester, England, in what should be a fun fight.

Neither man is currently lined up for a title shot, but if Parker wins this bout, there is every chance he can put his hand up.

Only Tyson Fury, Anthony Joshua, Deontay Wilder, Dillian Whyte, and Luis Ortiz are ahead of the Kiwi in the official ratings compiled by The Ring.

And with Fury vs. Joshua tying up the top two, that leaves a few options for Parker to get his horse back up and running.

If you’re looking to place bets on Chisora vs. Parker, I’ll explain how and where you can gamble on this fight later.

As one of the best boxing matches in May 2021, there is a lot of betting interest in this one. So, stay with me for that. 

Now, Chisora is coming to wage “War” on Parker. But will he live up to his ring moniker, or will he wilt in the Lancashire wind? That’s a good question, and one we will all find out on the night.

Chisora and Parker

Dmitry Bivol vs. Craig Richards

  • When: May 1, 2021
  • Where: Manchester Arena – Manchester, England
  • For: WBA (Super) Light Heavyweight Title

Fewer fighters in the game right now excite me as much as Dmitry Bivol.

The Russsian puts his 17-0 record as well as his world title on the line against London’s Craig Richards (16-1-1), in what will on the May Day Massacre on May 1.

It’s the first time the highly decorated former amateur fights in Britain, and what an opportunity to announce himself to what will be plenty of new fans.

If Bivol is fighting, I’m tuning in. But this bout should certainly be one of the best boxing matches to bet on, even if his opponent is in over his head.

If anything, I’m hoping this is a tuneup fight for a potential scrap with fellow-Russian, Artur Beterbiev later this year.

Now, that is going to be one of the fights of the decade, if it happens. But focusing on what’s in front of us, for now, this will be one of the top boxing bouts to gamble on in May.

Katie Taylor vs. Natasha Jonas

  • When: May 1, 2021
  • Where: Manchester Arena – Manchester, England
  • For: WBA, WBC, IBF, WBO, and The Ring Lightweight Titles

Ireland’s golden girl Katie Taylor takes on Natasha Jones on the Chisora vs. Parker undercard. If you are hoping to make money on the boxing, this will be another must-see bout in May 2021.

Taylor (17-0) is always popular with boxing betting fans and is a heavy favorite on the night.

The undisputed women’s lightweight champion takes on Britain’s Jonas (9-1), who recently fought to a split draw against WBC and IBO female super-featherweight champ, Terri Harper, in August 2020.

Like many of the fighters boxing in May, Taylor is essential viewing.

She commands a sizeable fanbase and will be looking to reward them with another convincing win, following controversy in her fights with Delfine Persoon in 2019 and 2020.

Chris Eubank Jr. vs. Marcus Morrison

  • When: May 1, 2021
  • Where: Manchester Arena – Manchester, England

If you’re tuning in for Chris Eubank’s return to the ring, you’ll be pleased to know it’s included in my top boxing matches to bet on in May.

Eubank takes the ropes for the first time since December 2019, now under the tutelage of all-time great, Roy Jones Jr. As it happens, Jones was once a rival of Eubank’s father, Chris Sr., although the pair never managed to get it on inside the ropes. 

The Brit is brimming with confidence ahead of his scrap with Morrison, and online boxing betting sites are feeling just as certain about his victory. Eubank is a massive favorite to win this fight.

You can find out where to get the best odds for Eubank vs. Morrison at the bottom of this page. But don’t miss the rest of the fights on this list.

So, if you’re looking for top boxing matches to bet on this month, make sure to pencil in Eubank’s return to the ring.

Andy Ruiz Jr. vs. Chris Arreola

  • When: May 1, 2021
  • Where: Dignity Health Sports Park – Carson, California

A battle of the more rotund heavyweights goes down on May 1 in California.

Well, these two have shed a lot of weight, so I’m not sure that tag still applies. Perhaps a battle of the premier Mexican American heavyweights is better.

But I am pretty sure if you think of heavy heavyweights, these two will probably be the first pair that comes to mind.

Arreola looks the more comfortable of the two, however. The three-time world title challenger has shed weight to push himself into the elite pack. But with a record of 2-2, he has a lot more to do. 

A convincing win over a former world champion in Ruiz would put Arreola in the spotlight. Especially Ruiz has been training with none other than pound-for-pound #1, Canelo Alvarez.

Canelo Alvarez vs. Billy Joe Saunders

  • When: May 8, 2021
  • Where: AT&T Stadium – Arlington, Texas
  • For: WBA (Super), WBC, WBO Super, The Ring Super Middleweight Titles

Betting on Alvarez to beat Saunders? Or perhaps you sense an upset win for the Brit in the 2021 Cinco De Mayo Weekend classic? 

Whatever way you are leaning, this fight is undoubtedly the biggest boxing match of May 2021.

It’s also the best fight to bet on this May, given the quality on show. Both fighters are world-class, but the consensus is that Saunders will struggle to deal with the flame-haired Mexican.

You can get my take on this one by reading my betting preview with the best odds for Canelo vs. Saunders, below.

Early Betting Preview of Canelo Alvarez vs. Billy Joe Saunders - May 8, 2021

Canelo Alvarez takes on Billy Joe Saunders in a super middleweight unification bout on May 8 at the AT&T Stadium in Arlington, Texas. Judging by the latest odds for Canelo vs. Saunders, it could be the toughest fight the flame-haired Mexican has had since...

Read More

Luis Nery vs. Brandon Figueroa

  • When: May 15, 2021
  • Where: Dignity Health Sports Park – Carson, California
  • For: WBC, WBA (Regular) Super Bantamweight Titles

There is no discussion about the best fights to bet on in May 2021 without bringing up this one.

Luis Nery vs. Brandon Figueroa should be an absolute classic, and certainly one you do not want to miss.

Not only does this one have “rematch” written all over it, but it could also have huge ramifications for a very healthy-looking super bantamweight division.

Nery (31-0) is top class, but he looked anything but his best in his last performance against Aaron Alameda in September 2020. His well-documented split with Eddy Reynoso as well as a few other questionable circumstances should give his opponent a lot to work with.

Is Nery physically and mentally prepared for that?

Well, the odds for Nery vs. Figueroa don’t suggest that anything major is up. But try to tell that to Figueroa (21-0), who is in great spirits following an excellent performance against Damien Vazquez in September. 

This is one of the boxing matches to bet on in May 2021 that could end up with honors at the end of the year.

Josh Taylor vs. Jose Ramirez

  • When: May 22, 2021
  • Where: Virgin Hotels Las Vegas – Paradise, Nevada
  • For: WBC, WBO, WBA (Super), IBF, The Ringlight-welterweight Titles

Josh Taylor could join his Celtic cousin in Katie Taylor as an undisputed champion if he can overcome the very tricky Jose Ramirez on May 22.

This is going to be one hell of a battle, and boxing bettors can get in on the action.

Once again, I’ll let you in on how and where to bet on boxing matches this May on the final section of this page. But for now, let’s carry with this fight.

Scotland’s Taylor (17-0) and America’s Ramirez (26-0) are both vouching to become the first undisputed king at 140 since Terence Crawford. Both are unbeaten, but the Edinburgh boy is a moderate favorite to get the win.

If Ramirez scores a win against Taylor, he is eyeing up a showdown with unified lightweight champion Teofimo Lopez. What a fight that would be, for both men.

Nordine Oubaali vs. Nonito Donaire

  • When: May 29, 2021
  • Where: TBA
  • For: WBC Bantamweight Title

It’s a case of third-time lucky for the upcoming WBC bantamweight title bout between Nordine Oubaali and contender Nonito Donaire.The fight will finally go down this May 29 at a venue that is yet to be announced.

To be honest, I don’t care if they fight in a cornfield in the Midwest, or a pub in Ireland, this is one of the top boxing fights to bet on in May.

Oubaali (17-0) was set to fight another man on this list, Lusi Nery, but that was scratched when Nery failed weight against Emmanuel Rodriguez.

That opened the door for legendary Filipino Donaire (40-6) to step up, and make his first appearance in the ropes since his Fight of the Year contender with Naoya Inoue in 2019.

There is talk that the winner could set up a match with Inoue at some point in the next year. But to be honest, I’m not looking past this one.

It should be an awesome contest to watch, and an interesting fight to bet on this May 2021.

Devin Haney vs. Jorge Linares

  • When: May 29, 2021
  • Where: Michelob Ultra Arena – Las Vegas, Nevada
  • For: WBC Lightweight Title

The excellent Devin Haney puts his WBC lightweight title against Jorge Linares in what could be a money-maker this May 29.

Haney (25-0) has long been criticized for avoiding top talent. He’s on the right track against Linares (47-5), even if the 35-year-old has seen better days.

But is a betting upset on the cards, or is “Dream” just too slick for the aging Venezuelan?

I’ll be providing my predictions and betting pick for Haney vs. Linares closer to the fight, as well as looking at who is next for the WBC champ. It was meant to be Ryan Garcia, until that (conveniently) fell apart.

Either way, this should be another top boxing bout to bet on this May.

Devin Haney

Betting on Boxing in May 2021

There you have the top ten boxing matches to bet on in May, but there are even more to get stuck into.

You can find odds for the fights on the best boxing sportsbooks, so sign up and get your bets down. If you are new to gambling on boxing, learning how to place a bet online is as easy as pie.

For the latest boxing predictions, picks, odds, and more, head over to the following sections of our site to get my take on the big fights.

I’ll bid you farewell for now. Good luck with those bets!

Adam Haynes
Adam Haynes

Adam is a sports writer and tipster with a strong background in MMA, boxing, and combat sports.

When Adam isn't writing about those, as well as politics, rugby, and Gaelic Games, he can be found working on methods and strategies to beat the bookies.

For his troubles, Adam is a fan of Leinster Rugby, Glasgow Celtic, and trusting the process.

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