In 1990, challenger James "Buster" Douglas shocked the boxing world when he knocked out Tyson in a fight most had thought would be over in one round.
Now the former heavyweight champion Douglas, now 58, has spoken about the stunning upset in Tokyo 28 years ago.
The edition of "30 for 30" aired on ESPN revealed just how one-sided the fight was expected to be.
Its title, "42 to 1", refers to the odds against a Douglas victory.
There was a background of personal tragedy before the fight, as Douglas had lost his beloved mother Lula Pearl just weeks before the fight.
Recalling his emotional post-bout interview, Douglas said: "It was good, it was motivating, the energy was flowing — until he asked me about my mum and it just broke it all down.
"That's when it really hit home."
Promoters held the fight in Japan because they didn't think anyone would want to watch it in the US.
John Johnson, Douglas' manager, said he took the fight to the far east because "no one would pay a penny for it here".
Some even dubbed the fight "30 Seconds Over Tokyo".
Tyson, 52, hadn't even been taken beyond the fifth round by any fighter since 1987.
Douglas was given so little chance of even going the distance that nearly every casino in Las Vegas refused to hold odds for the fight.
But as the bout went on, it was clear Douglas wasn't going to be like other fighters, unleashing a pummelling on the undefeated Tyson.
Tyson's crew were so unprepared for the fight they hadn't even brought an ice pack to stop the swelling.
"I knew I was here with no chance at all," Douglas told the interviewer.
"I knew that going into the fight no one was giving me a chance, but I believed, my people believed.
"That was the motivation. I could care less about what people though because if that was the case, I would have never turned pro."
Speaking about returning to Tokyo for the programme, Douglas said: "Just speaking of my mum, and then reliving it all, too, it just came back."
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