Riddick Bowe became the first fighter to defeat Evander Holyfield when he beat him in 1992 for the world heavyweight title. He then became the first fighter to knock Holyfield out, when he beat him in their rubber match in 1995. Bowe's professional boxing record stands at 43-1-0 (1 NC) with 33 KO's. He has defeated every opponent he has fought except Buster Mathis, Jr. (their bout ended as a no-contest). Bowe was ranked as the 21st greatest heavyweight of all time by Boxing Scene.
- 1983 at United States Junior Championships, as a middleweight, lost to Adolpho Washington by 2nd round TKO
- 1985 Junior World Champion as a light heavyweight, in competition in Bucharest. Defeated Péter Hart of Hungary in final.
- 1987 Heavyweight Bronze Medalist at Pan-American Games in Indianapolis. Lost to Jorge Luis Gonzalez on points
- 1988 Super Heavyweight Silver Medalist at 1988 Seoul Olympic Games. Results were:
- Defeated Biko Botowamungu (Zaire, Congo) KO 2
- Defeated Peter Hrivnak (Czechoslovakia) TKO 1
- Defeated Alex Miroshnichenko (Soviet Union) points
- Lost to Lennox Lewis (Canada) TKO by 2
Turning professional in March 1989, he knocked out novice (but future #1 contender) Lionel Butler. His manager Rock Newman kept Bowe active, fighting 13 times in 1989, beating journeymen, the most notable being Garing Lane, whom he beat twice. In September 1990 he made his first step up in class, fighting faded ex-champ Pinklon Thomas, who he dominated until Thomas was pulled out after 8 rounds. The following month he knocked out Bert Cooper in two rounds, which added to his reputation and high ranking. By the end of 1990 he had fought 8 times.
In March 1991 he overcame some rocky opening rounds to knock out the 1984 Olympic Super-Heavyweight Gold medallist Tyrell Biggs. However his image suffered when in his next fight, slick boxing ex-champ Tony Tubbs, whose own career had suffered with drugs and weight issues, appeared to outbox and outsmart Bowe, only to have the judges award Bowe with a unanimous decision that was jeered loudly by the crowd. In August 1991 he knocked out future champ Bruce Seldon in one round, and in July 1992 fought Pierre Coetzer in an eliminator, knocking out the durable South African in 7 rounds.
The fighters rematched two months later, with Bowe dominating and stopping Tillery - his first TKO loss.
Only a couple of weeks earlier in London, Bowe's old Olympic rival Lennox Lewis knocked out Canadian Donovan "Razor" Ruddock in 2 rounds, establishing himself as the WBC's #1 contender. The Bowe/Holyfield and Lewis/Ruddock fights were part of a mini-tournament where all four fighters agreed that the two winners would meet each other for the championship. Bowe's manager Rock Newman made a proposal that the $32 million purse HBO were offering be split 90-10 in Bowe's favor, an "absurd" offer which Lewis rejected. Lewis's manager Frank Maloney rejected another offer of $2 million for Lewis to fight on a Bowe undercard, citing his distrust of the Bowe camp after the aforementioned negotiations. So in a move that would hurt Bowe's image he held a press conference in which he dumped the WBC belt in a trash can rather than fight Lewis.
Bowe's first defense of his remaining titles came on February 6, 1993 when he fought 34-year-old former champion Michael Dokes at Madison Square Garden and knocked him out in the first round. In Bowe's next fight, May 22, 1993 at RFK Stadium in Washington, D.C., he knocked out Jesse Ferguson in the second round to retain the title. This set up a rematch with Evander Holyfield.
In the rematch with Holyfield, Bowe looked overweight. He had entered training camp at a 266 lbs and weighed in at 246 lbs, eleven pounds heavier than in the first fight with Holyfield.
Bowe and Holyfield exchanged hard punches, but Bowe ended up losing the belts to Holyfield by a majority decision. This fight was also known for a bizarre stunt in which parachutist James "Fan Man" Miller dropped into the open air arena, landing in the ropes by Bowe's corner. This surreal scene delayed the fight in the 7th round.