Gypsy Crusader vs King Azoulay turned into one of the most talked-about bouts of the weekend after the pairing headlined a chaotic influencer card in Orlando, Florida. The heavyweight kickboxing clash between online personalities Paul “Gypsy Crusader” Miller and Ben “King” Azoulay took place on the Duel Arena 1 card at the Kia Center, and it drew attention for reasons that went well beyond the sport itself.
Gypsy Crusader vs King Azoulay Fight Time and Venue
Fight time for the Duel Arena 1 event was set for Saturday, August 29, 2026, with the card starting around 8:00 PM ET at the Kia Center in Orlando, Florida. The Miller-Azoulay bout was billed as a co-main event on a heavyweight pro kickboxing rules basis, contested in a ring rather than a cage. Tickets for the event started at roughly $56.69, and the card was also made available to watch free-to-air after a change to the original lineup.
How the Card Came Together
Duel Arena’s inaugural show was originally supposed to be headlined by Mike Perry against Dillon Danis. However, Danis withdrew during fight week due to an injury and was replaced by middleweight veteran Brandon Jenkins. That change moved the card from a pay-per-view format to free viewing, shifting much of the promotional weight onto the Gypsy Crusader vs King Azoulay bout instead.
Weigh-In Numbers Before the Fight
Kickboxing weigh-ins ahead of the bout revealed a significant size gap between the two fighters. Paul Miller weighed in at 218lb, only slightly lighter than his 221lb weigh-in for a previous bout earlier in the year. Ben Azoulay, despite appearing in noticeably leaner shape, tipped the scales at 185.2lb, giving Miller more than a 30lb weight advantage heading into fight night. Florida’s athletic commission cleared the mismatch and confirmed the bout would go ahead as scheduled.
Backgrounds of the Two Fighters
Gypsy Crusader is the online alias of Paul Nicholas Miller, who first became known for Omegle livestreams featuring racist and antisemitic content directed at other users. He later pleaded guilty to unlawful possession of a firearm and ammunition and served a federal prison sentence before returning to combat sports. Miller holds a verifiable amateur record and had previously defeated fellow streamer Supah Hot Fire at a Brand Risk Promotions event earlier this year.
King Azoulay, whose real name is Ben Azoulay, built his following on TikTok and is known for viral, widely mocked claims such as saying he once fought thirty men at once. Unlike Miller, Azoulay has no verified professional record and had never competed in a sanctioned combat sports bout prior to this fight, with his prior bouts confined to influencer boxing cards.
Gypsy Crusader vs King Azoulay Fight Time Result
Fight time finally arrived after months of the matchup circulating online, having originally been floated for a July date in Nashville before being confirmed for the Duel Arena card. Azoulay made a theatrical entrance on a throne draped with an Israeli flag, embracing a villain role in front of a crowd that was largely supportive of Miller. Miller, by contrast, walked out with a serious demeanour, accompanied by MMA veteran Jake Shields.
Despite being significantly outweighed, Azoulay performed better than many expected, engaging Miller throughout the contest and even cutting his own shin during exchanges. Miller, however, used his experience and physical size advantage to control several exchanges, at one point catching and sweeping Azoulay to the canvas after a body kick attempt. The bout went the full distance, and one judge unusually scored the contest 29-28 in Azoulay’s favour, though Miller ultimately claimed the fight by split decision.
Duel Arena 1 Fight Card Summary
| Detail | Information |
|---|---|
| Event | Duel Arena 1: Perry vs Jenkins |
| Bout | Gypsy Crusader (Paul Miller) vs King Azoulay (Ben Azoulay) |
| Fight time | Saturday, August 29, 2026, approx. 8:00 PM ET |
| Venue | Kia Center, Orlando, Florida |
| Weight class | Heavyweight kickboxing |
| Miller weigh-in | 218 lb |
| Azoulay weigh-in | 185.2 lb |
| Result | Split decision win for Gypsy Crusader |
| Co-headliner | Mike Perry vs Brandon Jenkins |
Why This Fight Drew So Much Attention
Beyond the kickboxing itself, this bout became a major talking point because of how polarising both men are as internet figures. The Gypsy Crusader vs King Azoulay pairing was seen by many fans as a “freak show” attraction rather than a serious sporting contest, similar to other influencer fight cards that have gained popularity in recent years. The presence of Mike Perry on the same card, along with a late change in the main event, kept the overall show firmly in the spotlight leading into fight night.
Conclusion
The Gypsy Crusader vs King Azoulay fight time finally arrived on August 29 in Orlando, closing out months of online back-and-forth between the two personalities. Despite a considerable weight disadvantage, King Azoulay pushed the action further than expected, but Gypsy Crusader’s experience proved decisive as he came away with a split decision win on the Duel Arena 1 card.
Did the Gypsy Crusader win his fight?
Paul “Gypsy Crusader” Miller (real name Paul Miller) won his boxing debut against Supah Hot Fire by a controversial split decision on March 14, 2026.Â
Is Gypsy Crusader a good fighter?
Yes, Gypsy Crusader (Paul Miller) is a legitimately skilled and experienced former competitive kickboxer, though his recent celebrity-influencer bouts have drawn mixed and controversial receptions.Â
