- MIKE TYSON I
If it wasn’t for James “Buster” Douglas upsetting Mike Tyson, this would be considered THE Mike Tyson upset. Regardless, Holyfield bullied the bully for much of this November 1996 classic before putting Tyson out of his misery in the 11th round.
- RIDDICK BOWE II
Bowe and Holyfield combined to produce one of the greatest heavyweight trilogies, with Holyfield winning the second fight of the three – and his heavyweight championship back – in November 1993. Holyfield remains the only fighter to officially defeat Bowe.
- DWIGHT MUHAMMAD QAWI
In this July 1986 slugfest, Holyfield was forced to win his first cruiserweight belt the hard way when pushed to the limit for 15 rounds by an aggressive Qawi.
- GEORGE FOREMAN
Foreman, 42, was on the comeback trail when Holyfield outpointed him in April 1991. The win, not hugely appreciated at the time, grew in stature when Foreman regained the world heavyweight title three years later.
- MICHAEL MOORER II
Moorer had stripped Holyfield of his heavyweight titles in 1994, when outpointing him over 12 rounds, but was ruled out by the ringside physician after eight rounds in the pair’s rematch three years later. Moorer was down five times in all.
- BUSTER DOUGLAS
Unfortunately, Douglas showed up out of shape against Holyfield in October 1990 and was dealt with easily inside three rounds.
- MICHAEL DOKES
Done with cruiserweight, Holyfield ventured to heavyweight in 1988 and had his first proper test against the still dangerous Michael Dokes in March ’89. It was a test Holyfield passed with flying colours.
- CARLOS DE LEON
Eager to complete the set before moving to heavyweight, Holyfield won his third and final cruiserweight strap when he halted the underrated De Leon in April 1988.
- BERT COOPER
Many viewed Holyfield’s 1991 struggle with ‘Smokin’ Bert as evidence he would be destroyed by Mike Tyson as and when they met. With hindsight, this is one of Holyfield’s most thrilling wins at heavyweight.
- ALEX STEWART I
Again, another harder than anticipated bout at the time. But Stewart, then 24-0, gave it everything only to find Holyfield had significantly more, winning a forgotten thriller in eight rounds in 1989.