Evander Holyfield vs Riddick Bowe: ranking each fight from the epic heavyweight trilogy

If survival is one of the key traits needed to get to the top in boxing, Riddick Bowe and Evander Holyfield have demonstrated it in abundance throughout their glorious trilogy.

Between 1992 and 1995, the two teams brought out the best in each other – as Arturo Gatti and Mickey Ward would a decade later – elevating their reputations to near-mythical status in the division’s history.

Across 32 rounds in Las Vegas, they delivered world titles, blood, sweat, drama, and even an unexpected airborne visitor.

Ranking the three battles from worst to best seems almost sacrilegious – like choosing a favorite movie 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)

Their rematch 12 months after their first meeting saw another bruising battle – and a memorable interruption when parachutist James Miller crash-landed on the ring, causing a 20-minute delay. Once order was restored, the heavyweight duo once again brought out the best in each other.

But this time, “The Real Deal” combined his ring smarts with his natural fighting instincts. Bowe, weighing 11 pounds, started fast and landed a right hand, while Holyfield, trying to keep his distance, couldn’t resist trading in the fourth.

Bowe was cut off and Holyfield took control, but soon found himself on shaky legs. Heated discussions after the bell added to the chaos. In the later rounds, Holyfield’s reliable left hook repeatedly hurt Bowe, and although “Big Daddy” fought bravely until the final bell, his 12-month reign as champion was over. Bowe was full of praise for his opponent in the post-fight press conference.

“Wasn’t Evander great? We can’t take anything from Evander. He deserves it.”

2: November 4, 1995 – Bowe vs. Holyfield 3 (Bowie wins by stoppage in round 8)

The only non-title match in the trilogy – and the only one that did not 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 lively third round, “The Real Deal” appeared on the verge of victory in the sixth round when he dropped a left hook and an upper right to the big man. But after emptying the tank, he was unable to finish the job, allowing Poe to recover. Trainer Eddie Futch warned his fighter to avoid Holyfield’s left hook, but in the eighth round, as the two men traded again, fatigue left Holyfield open.

Bowe landed a crushing right that sent him crashing to the ground, and although Holyfield somehow rose, two overhand rights sent him back down. Referee Joe Cortez waved it off, ending one of boxing’s greatest trilogies. Next, Bowe discussed the first knockout of his career.

“I was thinking the same thing he was thinking. ‘Hell, this isn’t true.’

1: November 13, 1992 – Bowe vs. Holyfield I (Bowie wins by unanimous decision: 115-112, 117-110, 117-110)

Where it all started. With a 30-pound weight disadvantage to overcome, Evander Holyfield did everything he could to retain his undisputed heavyweight title against Riddick “Big Daddy” Bowe in their first meeting. They were both undefeated and that had to change. Despite the defeat, Holyfield’s courage helped produce one of the most exciting heavyweight fights ever.

Expecting Bowe to fade late, the champion found himself stunned by a big right uppercut in the 10th. On the brink of collapse, Holyfield dug deep and fired off ferocious combinations to end the round.

But on the 11th, he fell with a right hand, and although he somehow survived to hear the bell, the end was inevitable. Bowe took a unanimous decision and captured the championship, while Holyfield, ever the warrior, summed it up perfectly afterward:

“In the 10th round he hit me post to post. He thinks he owns me, and I think I own him.”

Trying to rank the three fights seems almost disrespectful. Each offered something different but equally memorable – from the raw brutality of the first, to the chaos and redemption of the second, to the emotional final act of the third.

Riddick Bowe and Evander Holyfield didn’t just give us a hat-trick, they gave us a benchmark.