The Unlikeliest Victories: Revisiting Sports' Biggest Shocks

Look, everyone loves an underdog story. It’s why we watch, right? But some upsets aren’t just underdogs barking; they’re full-blown meteor strikes. I’ve seen my share of "shockers" over the years, but a few stand above the rest, the ones where the script was not just flipped, but shredded.

Let’s kick it off with the one that still makes bookmakers sweat: Leicester City winning the Premier League in the 2015-2016 season. Their opening odds were a staggering 5000/1. To put that in perspective, the odds of finding Elvis alive were shorter. Jamie Vardy, Riyad Mahrez, and N'Golo Kanté led a team that avoided relegation by the skin of their teeth the year before, then finished atop England’s toughest league with 81 points, ten clear of second-place Arsenal. That wasn't just a win; it was a cultural phenomenon.

Then there’s the "Miracle on Ice." February 22, 1980, Lake Placid, New York. The U.S. men’s Olympic hockey team, a squad of college kids and amateurs, faced the seemingly invincible Soviet Union team, who had won the previous four Olympic gold medals and outscored opponents 51-11 in the 1976 Games. The Soviets had crushed the U.S. 10-3 in an exhibition just days before. But Jim Craig made 36 saves, Mike Eruzione scored the game-winner in the third period, and the Americans pulled off a 4-3 victory. They then went on to beat Finland 4-2 to claim gold.

Boxing has delivered some absolute jaw-droppers, none bigger than Buster Douglas knocking out Mike Tyson on February 11, 1990, in Tokyo. Tyson was 37-0, undisputed heavyweight champion, and a 42/1 favorite. Douglas, a fringe contender, was supposed to be a tune-up. Instead, he absorbed Tyson’s power, dished out his own, and delivered an uppercut in the tenth round that sent Tyson to the canvas for the first time in his career. The ref counted him out at 1:23 of that round. People still talk about Evander Holyfield beating Tyson, but Douglas did it first and against a truly prime "Iron Mike."

International football has a knack for these moments. Greece winning Euro 2004 is right up there. They entered the tournament in Portugal as 150/1 outsiders. Their style of play under Otto Rehhagel was hardly beautiful, but it was effective. They beat the host nation, Portugal, 1-0 in the opening game, then again 1-0 in the final on a headed goal from Angelos Charisteas. Greece had never won a major tournament game before 2004, let alone the whole thing.

Here’s the thing: sometimes the upset comes from a single race or game. Think about Rich Strike, who won the 2022 Kentucky Derby at 80/1 odds. He wasn't even in the race until Friday morning when a scratch opened up a spot. He broke from post 21, last into the first turn, and then exploded down the stretch under jockey Sonny Leon to win by three-quarters of a length, paying $163.60 for a $2 win bet. It was the second-longest shot to ever win the Derby.

Super Bowl XLII on February 3, 2008, saw the New York Giants, 12-point underdogs, defeat the undefeated New England Patriots 17-14. The Patriots were 18-0, chasing a perfect season, and had beaten the Giants 38-35 in the regular season finale. Eli Manning and David Tyree’s "helmet catch" in the final minutes set up Plaxico Burress’s game-winning touchdown with 35 seconds left. That crushed a lot of parlays, let me tell you.

And let's not forget the 1969 New York Mets, "The Amazin' Mets." They finished ninth in the ten-team National League in 1968. In '69, they were 100/1 to win the World Series. Led by Tom Seaver and Jerry Koosman, they shocked the heavily favored Baltimore Orioles, winning the Series in five games, taking Game 5 by a 5-3 score on October 16. That team captured the heart of the city.

One more for the road: Appalachian State beating No. 5 Michigan 34-32 on September 1, 2007. A Division I-AA (now FCS) team going into the Big House and beating a national powerhouse. It was the first time an FCS team ever beat a ranked FBS team, and it sent shockwaves through college football. Corey Lynch blocked a 37-yard field goal attempt on the final play to seal the win.

Real talk: I still think Leicester City is the biggest upset of them all. Sustained brilliance over a 38-game season at 5000/1? That's just absurd.

My bold prediction? We’ll see another 1000/1 longshot win a major sporting event within the next decade. It’s what keeps us watching.