He was favored to win the light-heavyweight championship at the 1984 Los Angeles games, but instead received a bronze medal after a controversial end in the semifinals to his Olympic dreams of gold. After virtually knocking out New Zealand's Kevin Barry with just seconds left in the second round, the referee accused Holyfield of hitting after the break and disqualified him.

During the medal ceremony, the crowd cheered wildly for Holyfield and, in a true display of good sportsmanship, the recipient of the gold medal pulled him up to the top step and raised his hand.

Holyfield relied heavily on his faith and on the values of respect and perseverance instilled in him by his mother to accept the ruling. He had learned to expect the inevitability of setbacks in life, knowing that they could not cause him to give up. When he was a child his mother had told him, "If you start quitting, you'll be quitting for the rest of your life, because nothing is going to go your way all the time." He knew that he could only achieve his goals if he believed in himself, worked harder, and did not quit. His poise under the strain of such an obvious disappointment set the tone for his demeanor during his professional career.

Just months after the Olympics, Holyfield made his professional debut by defeating Lionel Byarm. He won four bouts in the Junior Heavyweight Division before moving up to Cruiserweight, where he continued to dominate. He won his first world title in 1986 against the WBA's world Cruiserweight champion Dwight Qwai.

To this day, Holyfield is the only undefeated, undisputed Cruiserweight Champion.

On October 25, 1990, Holyfield fulfilled his lifelong dream of becoming the Heavyweight Champion of the World when he dropped James "Buster" Douglas – then IBF, WBC and WBA Champion – in three rounds. Holyfield was the first cruiserweight champion to win the heavyweight title.

Immediately after accomplishing such an amazing feat, Holyfield prayed, thanking God for letting him reach his goal, acknowledging that he couldn't have done it without Him. When asked to sign autographs, Holyfield happily did so, and revealed the source of his strength, also writing the reference "Phil. 4:13." The message refers to the scripture in the book of Philippians, which states "I can do all things through Christ which strengtheneth me."

His first title defense was against George Foreman, who'd had sixty-five knockouts in his sixty-nine victories – with ten of those KO's occurring in the last two years. The bout against Foreman ended after twelve rounds, with Holyfield retaining his title.

 Holyfield was more than ready to fight Mike Tyson. After much wrangling between their promoters, the fight was scheduled for November 8, 1991. It was the most anticipated match of the season. The reigning champ began an intense training regimen for the title defense, but on October 18, the bout was cancelled when Tyson injured his ribs.