If survival is one of the key traits needed to reach the very top in boxing, then Riddick Bowe and Evander Holyfield showcased it in abundance throughout their glorious trilogy.
Between 1992 and 1995, the two heavyweights brought out the very best in each other — much like Arturo Gatti and Micky Ward would a decade later — elevating their reputations to near-mythic status in the history of the division.
Across 32 rounds in Las Vegas, they delivered world titles, blood, sweat, drama, and even an unexpected airborne visitor.
To rank the three fights from worst to best feels almost sacrilegious — like choosing a favourite film from a beloved trilogy. You probably know the answer deep down, but you don’t enjoy admitting it.
3: November 6, 1993 – Bowe vs Holyfield II (Holyfield wins by majority decision: 115-113, 115-114, 114-114)
The rematch 12 months after their first meeting delivered another bruising battle — and an unforgettable interruption when parachutist James Miller crash-landed on the ring, causing a 20-minute delay. Once order was restored, the two heavyweights once again brought out the best in each other.
This time around, though, ‘The Real Deal’ combined ring intelligence with his natural fighting instincts. Bowe, 11 pounds heavier, started fast and landed thudding right hands, while Holyfield, trying to keep his distance, couldn’t resist trading in the fourth.
Bowe was cut and Holyfield took control, but soon found himself on shaky legs. Heated exchanges after the bell only added to the chaos. In the later rounds, Holyfield’s trusted left hook repeatedly hurt Bowe, and though ‘Big Daddy’ battled bravely to the final bell, his 12-month reign as champion was over. Bowe was full of praise for his rival at the post-fight press conference.
“Wasn’t Evander great? We can’t take anything away from Evander. He deserves it.”
2: November 4, 1995 – Bowe vs Holyfield III (Bowe wins by eighth round stoppage)
The only non-title bout of the trilogy — and the only one not to go the distance — was billed as “The Final Chapter.” A knockout always felt inevitable as Holyfield set a frenetic pace, choosing to trade rather than box.
After a pulsating third round, ‘The Real Deal’ appeared on the brink of victory in the sixth when a left hook and overhand right dropped the big man. But having emptied the tank, he couldn’t finish the job, allowing Bowe to recover. Trainer Eddie Futch warned his fighter to avoid Holyfield’s left hook, yet in the eighth, as the two men traded once more, exhaustion left Holyfield open.
Bowe landed a crushing right that floored him, and though Holyfield somehow rose, two overhand rights sent him down again. Referee Joe Cortez waved it off, ending one of boxing’s greatest trilogies. Afterwards, Bowe discussed the first knockdown of his career.
“I was thinking the same thing he was thinking. ‘Hell, this ain’t right.’”
1: November 13, 1992 – Bowe vs Holyfield I (Bowe wins by unanimous decision: 115-112, 117-110, 117-110)
Where it all began. With a 30-pound weight disadvantage to overcome, Evander Holyfield did everything he could to retain his undisputed heavyweight crown against Riddick ‘Big Daddy’ Bowe in their first meeting. Both were undefeated and that had to change. Despite defeat, Holyfield’s courage helped produce one of the most thrilling heavyweight battles ever staged.
Expecting Bowe to fade late, the champion instead found himself staggered by a right uppercut in the 10th. On the brink of collapse, Holyfield dug deep and fired back with ferocious combinations to end the round.
But in the 11th, he was sent tumbling by a right hand, and although he somehow survived to hear the bell, the end was inevitable. Bowe took a unanimous decision and the championship, while Holyfield, ever the warrior, summed it up perfectly afterwards:
“In the 10th round he knocked me from pillar to post. He thinks he has me; I think I have him.”
Trying to rank the three fights feels almost disrespectful. Each offered something different yet equally unforgettable — from the first’s raw brutality, to the second’s chaos and redemption, to the third’s emotional final act.
Riddick Bowe and Evander Holyfield didn’t just give us a trilogy — they gave us a benchmark.