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Evander Holyfield

1990-92, 1993-94

The only man to win a heavyweight title four times, Holyfield won the lineal championship on two occasions during his career. A former cruiserweight world champion, he toppled James "Buster" Douglas in 1990 to win the heavyweight championship and defended three times before losing to unbeaten Riddick Bowe in 1992. Holyfield won the rematch in 1993 (the infamous "Fan Man" bout) but lost the championship to Michael Moorer the following year.

Despite going on to claim multiple alphabet titles, Holyfield fought for the lineal crown just twice more, losing to Lennox Lewis in a 1999 title unification bout eight months after their first meeting ended in a controversial split draw.