He turned professional at the age of 21, moving up to cruiserweight in 1985 and winning his first world championship the following year, defeating Dwight Muhammad Qawi for the WBA title.

Holyfield then went on to defeat Ricky Parkey and Carlos de León to win the WBC and IBF titles, thus becoming the undisputed cruiserweight champion.

He successfully defended his titles three times, scoring victories over former champions George Foreman and Larry Holmes, before suffering his first professional loss to Riddick Bowe in 1992.

In 1999 he faced Lennox Lewis in a unification fight for the undisputed WBA, WBC, and IBF titles, which ended in a controversial split draw.

[10] Holyfield describes himself as a physical "late bloomer": upon graduating from Fulton High School in 1980, he was only 5 ft 8 in (1.73 m) tall and weighed only 147 pounds (67 kg).

When he was 20 years old, Holyfield represented the U.S. in the 1983 Pan American Games in Caracas, Venezuela, where he won a silver medal after losing to Cuban world champion Pablo Romero.

The following year, he was the National Golden Gloves Champion, and won a bronze medal in the 1984 Summer Olympic Games in Los Angeles, California, after a controversial disqualification in the second round of the semi-final against New Zealand's Kevin Barry.

[12][13][14] Holyfield started out professionally as a light heavyweight with a televised win in six rounds over Lionel Byarm at Madison Square Garden on November 15, 1984.

In what was called by The Ring as the best cruiserweight bout of the 1980s, Holyfield became world champion by defeating Qawi by a narrow 15 round split decision.

In 1987, he defended his title against former Olympic teammate and Gold medal winner Henry Tillman, who had beaten Mike Tyson twice as an amateur.

Having suffered the first technical knockdown of his professional career, Holyfield regained his composure quickly and administered a beating that left Cooper still on his feet, but unable to defend himself.

Holyfield landed brutal power shots, culminated by repeated vicious uppercuts that snapped Cooper's head back.

In what is considered by many sporting historians as one of the most bizarre moments in boxing's history, during round seven the crowd got off their feet and many people started to run for cover and yell.

It later surfaced that the chairman of the medical advisory board for the Nevada State Athletic Commission believed his condition to be consistent with HGH use.

Tyson's teeth tore off a small section of the top of his opponent's ear, known as the helix, and spat that bit of flesh out onto the canvas.

Holyfield knocked Moorer to the canvas five times and referee Mitch Halpern stopped the fight between the eighth and ninth rounds under the advice of physician Flip Homansky.

In 1998 Holyfield had only one fight, making a mandatory defense against Vaughn Bean, who was defeated by decision at the Georgia Dome in the champion's hometown.

2002 began as a promising year for Holyfield: in June, he met former World Heavyweight Champion Hasim Rahman, to determine who would face Lewis next.

Holyfield was initially criticized for his ongoing comeback; but he was adamant that his losses to Toney and Donald were the result of a shoulder injury, not of old age.

Holyfield had looked better in his first four fights since Donald and appeared to have answered the critics who say that he lacked the cutting edge and ability to follow up on crucial openings that he had in his youth.

Although unable to defy his critics by winning a fifth Heavyweight title, Holyfield refused to be backed up by the young champion and even rattled him in the closing part of the 12th round.

On December 20, 2008, he fought, at the Hallenstadion in Zürich, Switzerland, the WBA Heavyweight Champion Nikolai Valuev for a paycheck of $600,000, the lowest amount he has ever received for a championship fight.

"[31] The American boxer scored an eighth-round knockout of Botha to win the vacant World Boxing Federation (WBF) Heavyweight title.

[35][36] Holyfield's next bout against Sherman "The Tank" Williams on November 5, 2010, at Joe Louis Arena in Detroit, Michigan, was then postponed twice before finally being rescheduled to January 22, 2011, and moved to The Greenbrier in White Sulphur Springs, West Virginia.

Holyfield started the fight aggressively, pressing the 46-year-old Nielsen into the ropes and landing several hard jabs and hooks, knocking him down in the 3rd round.

[40][41] After the Nielsen fight, Holyfield attempted to land a shot at a world heavyweight title (all major belts were held by Wladimir and Vitali Klitschko, at that time).

[44] In 2015, Evander Holyfield and Mitt Romney participated in a friendly exhibition bout for charity; the event took place in Utah to help the organization CharityVision.

[45] On April 16, 2021, it was announced that Holyfield would return to the ring on June 5, 2021, to face Kevin McBride (most widely known for defeating former undisputed heavyweight champion Mike Tyson) in an exhibition bout on the undercard of Teófimo López vs. George Kambosos Jr.[46] However, after the López vs. Kambosos card was postponed multiple times, the fight against McBride ultimately did not materialize, leading Holyfield to file a demand for arbitration against Triller.

On August 13, 2007, Holyfield was confirmed to participate in a boxing match at World Wrestling Entertainment's Saturday Night's Main Event XXXV against Matt Hardy.

His fortune was drained by frivolous spending, multiple failed business ventures, constant child support payments, and his three divorces, among other things.