Evander Holyfield Timeline

In 1988, Holyfield started the year by becoming the first universally recognized World Cruiserweight Champion after defeating Lineal & WBC Champion Carlos De León at Las Vegas. He later beat former Heavyweight Champion Pinklon Thomas by knockout in seven rounds in his third and final bout of 1988.

Image source: Evander Holyfield vs. Carlos De León

Holyfield began 1989 meeting another former Heavyweight Champion, Michael Dokes, as he continued building toward a shot at the undisputed heavyweight championship.

In 1990, Holyfield beat Seamus McDonagh, knocking him out in four rounds. Holyfield had been promised a title shot against Mike Tyson in 1990.

On October 25, 1990, Holyfield defeated Buster Douglas to claim the unified WBA, WBC and IBF heavyweight titles and become the undisputed heavyweight championship holder, making him the only four-time world heavyweight champion lineage's start.

Image source: Buster Douglas vs. Evander Holyfield

Holyfield successfully defended his unified titles three times, scoring victories over former champions George Foreman and Larry Holmes. A deal was signed for him to defend his crown against Mike Tyson in November 1991. In his first fight of 1992, he faced 42-year-old former world heavyweight champion Larry Holmes.

In the beginning of a trilogy of bouts with the 25-year-old Riddick Bowe, who had won an Olympic silver medal in 1988, Holyfield suffered his first defeat when Bowe won the undisputed title by a 12-round unanimous decision in Las Vegas.

Image source: Evander Holyfield vs. Riddick Bowe

Holyfield began 1993 by beating Alex Stewart in a rematch, this time over the 12-round unanimous distance.

Then came the rematch with Bowe on November 6, 1993. Holyfield's victory over Bowe helped him be named ABC's Wide World of Sports Athlete of the Year for 1993. However, he later lost these titles in an upset against Michael Moorer.

In April 1994, Holyfield met former WBO light heavyweight Michael Moorer, who was attempting to become the first southpaw to become the universally recognized world heavyweight champion, and lost his titles in the upset. Holyfield was then forced to retire upon medical advice, only to return a year later with a clean bill of health.

Image source: Evander Holyfield vs. Michael Moorer II

In 1995, Holyfield returned to the ring with a ten-round decision win versus former Olympic gold medalist Ray Mercer.

In 1996, Holyfield defeated Mike Tyson by TKO in round 11 and reclaimed the WBA title, in what was named by The Ring magazine as the Fight of the Year and Upset of the Year.

Image source: Evander Holyfield vs. Mike Tyson II

Holyfield's rematch with Tyson took place on June 28, 1997. Holyfield won the 1997 rematch by disqualification in round three after Tyson bit both of Holyfield's ears. Holyfield also held the IBF title a third time from 1997 to 1999 during this reign.

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.

In 1999, the public clamored for a unification bout versus WBC World Champion Lennox Lewis of the United Kingdom. The fight ended in a controversial split draw, leaving the undisputed championship unresolved.

Image source: Evander Holyfield vs. Lennox Lewis

In 2000, Lewis was stripped of the WBA belt for failing to meet lightly regarded Don King fighter John Ruiz, having fought Ruiz's conqueror David Tua, and the WBA ordered Holyfield and Ruiz to meet for that organization's world title belt. Holyfield won, beginning his fourth WBA title reign from 2000 to 2001.

Image source: Evander Holyfield vs. John Ruiz

Seven months later, in March 2001, it was Ruiz's turn to make history at Holyfield's expense when he surprisingly managed to knock Holyfield down and beat him by a 12-round decision to become the first Hispanic ever to win a Heavyweight title.

Image source: Evander Holyfield vs. John Ruiz II

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.

On December 14, 2002, Holyfield once again tried to become the first man ever to be Heavyweight Champion five times when he and Chris Byrd met, but Byrd came out as the winner by a 12-round unanimous decision.

Image source: Evander Holyfield vs. Chris Byrd

On October 4, 2003, Holyfield lost to James Toney by TKO when his corner threw in the towel in the ninth round.

Image source: Evander Holyfield vs. James Toney

At age 42, Holyfield returned to the ring to face Larry Donald on November 13, 2004.

In August 2005 it had been reported that the New York State Athletic Commission had banned Evander Holyfield from boxing in New York due to "diminishing skills" despite the fact that Holyfield had passed a battery of medical tests.

Holyfield defeated Jeremy Bates by TKO on August 18, 2006, in a 10-round bout at American Airlines Center in Dallas, Texas, then defeated Fres Oquendo by unanimous decision on November 10, 2006, in San Antonio, Texas.

On March 17, 2007, Holyfield defeated Vinny Maddalone by TKO when Maddalone's corner threw in the towel to save their man. On June 30, 2007, he defeated Lou Savarese, knocking the bigger and heavier Savarese down in the fourth and again in the ninth round, en route to a unanimous decision win.

On October 13, 2007, Holyfield was defeated by Sultan Ibragimov, ending hopes of another title run.

Image source: Sultan Ibragimov vs. Evander Holyfield

On December 20, 2008, Holyfield fought at the Hallenstadion in Zürich, Switzerland, against WBA Heavyweight Champion Nikolai Valuev for a paycheck of $600,000, the lowest amount he has ever received for a championship fight. There was talk of a rematch in 2009.

Image source: Nikolai Valuev vs. Evander Holyfield

He reportedly agreed to fight South African boxer Francois Botha; it was agreed the venue would be Nelson Mandela Memorial Stadium in Kampala, Uganda. A few weeks before the fight, it was revealed the bout would be postponed to February 20, 2010.

The match with Francois Botha was put in jeopardy due to economic disagreements but was later confirmed to be on April 10, 2010, at the Thomas & Mack Center in Las Vegas.

Image source: Mike Tyson vs. Evander Holyfield

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

A fight with Brian Nielsen, the most popular Danish heavyweight in that country's history, was scheduled for March 5, 2011, in Denmark, but needed to be postponed to May 7, 2011, due to a cut Holyfield received in the Williams fight. This became his final professional bout, ending a career spanning 1984 to 2011.

After more than a year of trying to land fights, Yahoo News reported his intention to retire in 2012, with Holyfield stating, "The game's been good to me and I hope I've been good to the game." However, in June 2014, after not fighting in over three years, Holyfield announced his final retirement. He is ranked number 77 on The Ring's list of 100 greatest punchers, and in 2002 The Ring named him the 22nd greatest fighter of the past 80 years.