Tyson vs Douglas..... Greatest upset in boxing history at least from an odds perspective... 40 to 1....that says it all.
It doesn't quite say it all, because it misses out the fact that Tyson-Douglas was not within the last 20 years.
I think too many people on here are overlooking the fact that Thomas Hearns started his world title career at welterweight (147lbs), yet a decade later took the zero of the undefeated lightheavyweight champion (175lbs). Is it just me, or this is a much better win than any other win mentioned so far on this thread (that was within the last 20 years)?
Good one.... First MW to grab the HW title in over 100 yrs. James Toney did as well but that was tainted.
Which is exactly what made it one of the best "single" wins. Douglas became great for that one event to pull off the greatest upset in boxing history. The sports world was upside down come Feb 11 1990.
Douglas' win over Tyson was almost 23 years ago. Don't qualify for the title of your OP other wise LSpinks over Ali would be better. I'll go with Holy KOing Tyson in their first fight. He was nearly as big an underdog as I've ever seen(the odds closed to a little closer to 7-1 by fight time) and he proceeded to disassemble the LEGEND that was Mike Tyson, proving, the vulnerabilities exposed by Douglas were still there. Best win ever over a prime, nearly unstoppable foe.
Tyson wasn't prime or unstoppable....his fantastic win against Frank Bruno papered over the cracks that he wasn't the same man after prison....Douglas if the thread read (in the last 25 yrs) but I have to go with George Foreman v Michael Moorer.... nobody and I mean nobody saw that coming! But also Hopkins V Tito was a massive perfomance so I go with Foreman for the victory but Hopkins for the performance Lol
Good win but It's just Ruiz Joppy? C'mon Jay Nady won that fight, not overrated Chavez Guy that started at light heavyweight vs a blown up welterweight. Lucky Punch, lost the first round. Barerra had to close his gym for 4 weeks before the fight.