When Conor McGregor and Max Holloway last shared a cage, the calendar read August 17, 2013, and the bout served merely as a preliminary stepping stone ahead of a Chael Sonnen and Mauricio Rua main event. McGregor walked away with a unanimous decision victory, extending a streak that would eventually touch 15 fights, while Holloway absorbed the third loss of his burgeoning UFC career. Thirteen years later, the context has completely inverted. The preliminary scrap has transformed into the marquee main event of UFC 329 at T-Mobile Arena in Las Vegas.

The market reflects the profound passage of time and contrasting activity levels. Early odds opened with Holloway installed as a commanding -400 favorite, a figure that has since settled closer to -220 at operators like BET99, translating to an implied win probability of roughly 68.8%. Meanwhile, McGregor's return from a five-year hiatus—accelerated by a broken leg against Dustin Poirier in 2021, legal complications, and a lengthy drug-testing suspension—has drifted down to +165 for the outright upset.

Alex Rella, Trading Manager at BetMGM, captured the overarching sentiment of the bookmaking room: Conor McGregor in his prime was truly awesome, but he hasn't fought since 2021. Who knows what version of Conor is going to show up? On the other hand, Max Holloway has never stopped being an elite fighter. There are few fighters in the world that can beat Max in a straight-up striking battle.

Advertisement

The Activity Gap and Tactical Realities

While McGregor has remained on the sidelines nursing injuries and navigating inactivity, Holloway has stayed firmly entrenched in the organizational churn. The Hawaiian has logged eight UFC appearances since McGregor's last walk to the Octagon, going 5-3 against top-tier competition, most recently dropping a unanimous decision to Charles Oliveira at UFC 326. That sustained presence creates a steep tactical hurdle for a 37-year-old fighter attempting to reintegrate himself at championship pace.

As analyst Joe Osborne bluntly noted regarding the matchup's structural arc: While envisioning an upset win over Max Holloway is fun, it’s also delusional. Coming off a five-year layoff, we shouldn’t expect an improved version of McGregor at 37 years old. He won’t be able to compete with the striking volume and pace of Holloway, who’s a year removed from a one-sided victory over Poirier. The longer the fight goes, the worse McGregor will look. Expect a Holloway TKO victory.

Market Mechanics and Public Money

The betting behavior surrounding this rematch mirrors the hallmarks of McGregor's career peak. Heavy public interest routinely drives money onto the charismatic star, artificially shortening his underdog price while offering better value for those backing the disciplined favorite. Market watchers note that waiting out the line often yields the most favorable entry point on Holloway as public liability mounts.

Sources

These sources formed the evidence pack for this article. Links open the original publisher; inclusion does not imply endorsement.

  1. covers.com original
  2. sportsgambler.com original
  3. nypost.com original