The Top Ten Sports Upsets of the Last 20 Years

By David “Large” Larzelere
It’s difficult to truly comprehend the impact of a great sports upset through a historical lens. To really feel an upset’s magnitude, you have to go into a fight or match or game as a fan and feel that you wouldn’t lay a sawbuck down on the underdog even if the odds were 200 to 1, and not because you’re not a gambling man but because you just see no reason to waste a perfectly good sawbuck.
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With that in mind, just for today I’d like to ignore the Super Bowl III’s and Clay/Liston’s and rank yesterday’s upset on a more contemporary scale. The dates are arbitrary, of course, the last 20 years, perfect for a list written by a thirty-something such as myself. I’ve limited the candidates to playoff games, championships, title fights, etc., to raise the stakes beyond a question of mere gambling odds. The criteria is simply my own memory and sense of improbability at the time. So without further ado I present to you my Top Ten Sports Upsets of the Last 20 Years.
10. UConn over Duke, 1999 NCAA men’s basketball final – This narrowly nabbed my ten-spot over the 1990 World Series. Huskies were 10-point dogs, feels like more in retrospect.
9. Senegal over France, 2002 World Cup – A former colony knocks its colonizers, also the defending World Cup champions, out of the World Cup. Better upsets are on this list, but not many better stories.
8. Nuggets over the Sonics, 1994 playoffs – Two games down to the best team in the NBA and the hapless, barely .500 Nuggets come back and do the Sonics in five. At 0-2 I wouldn’t have bet the change in my pocket on them.
7. Pistons over the Lakers, 2004 NBA Finals – Denver over Seattle was a bigger upset, but this was the Finals. At the time, it was understood as hands down the biggest upset in NBA Finals history. It didn’t feel quite that mammoth to me, but it was still pretty mammoth.
6. Duke over UNLV, 1991 Final Four – Undefeated Tark and the gang with pretty much the same squad that had spanked the Dukies by 30 in the ’90 Finals. At the time, it felt almost as big as Villanova/Georgetown.
5. Hasim Rahman over Lennox Lewis, 2001 – No, Lewis did not have quite the aura of invincibility that say, Tyson did (more on him later), but this was still an all-time mind-bender. Rahman was 20 to 1, and over 100 to 1 in my memory to win it in five rounds or less.

4. Patriots over Rams, Super Bowl XXXVI – The Greatest Show on Turf grounded. I never saw it coming. I lost money on this one actually, only thing on the list other than UConn/Duke that took my cash (and let me just add that if Spygate turns up some real dirt on this, I fully expect a refund on that.)
3. Rulon Gardner over Alexander Karelin, Greco-Roman gold medal match, Sydney Olympics – I was at the Sydney Games with NBC. We watched all of Karelin’s matches in the research room just to see him wreck dudes. To sum up, the man hadn’t lost a match in 13 years and pretty much made dudes crap themselves when they faced him. Meanwhile, Gardner was nobody. It wasn’t exactly a thrilling victory – it was actually kind of hard to figure out why Rulon won. But the fact that he did was unthinkable.
2. Giants over Patriots, Super Bowl XLII – Yes, number two. I know it’s the day after, and maybe it will fade with time, but I’m telling you, this one seemed about as in the bag to me as anything I’ve ever watched sports-wise. I didn’t actually believe it until I saw it, and even then I didn’t believe it. I still don’t quite believe it.
1. Buster Douglas over Mike Tyson, 1990 – You can have all the Super Bowl III’s and Miracles on Ice you want – I still think this is number one all-time. That Douglas was a 42-1 underdog is an oft-cited fact, but what you rarely hear is that those bookies who were taking Tyson action were generally taking it at around 1-200. Two hundred dollars buys you one. And even with that rate of exchange, a LOT of people dropped big coin on Iron Mike that night.↵