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howardRandy Turpin over Sugar Ray Robinson in 1951 was a huge upset. Douglas over Tyson is up there but in retrospect that outcome is not as shocking as it was at the time. Tyson had probably already started on his downward spiral and Buster Douglas was a pretty good fighter when motivated. The knock on him was that he was lazy which he proved when he went into his next fight horribly out of shape and got his ass handed to him by Evander Holyfield.