Leicester City -- and the biggest sports upsets ever

5,000-1!!!!

On this day in 2016, the most stunning longshot in sports history came home: Leicester City, a little-regarded English soccer club, won the Premier League title.

It’s hard to even describe — especially to non-soccer fans — the immensity of the upset that Leicester’s championship constituted.

The English Premier League is the top league in all of world soccer. It is filled with stars — and money. And, it is typically dominated by a handful of the wealthiest — and most well known — clubs in the world: Manchester City, Arsenal, Manchester United, Chelsea and Liverpool. Since 2000, one of those five clubs has won the title every single year — but one.

The one is Leicester, who in the 130+ year history of the club, has won just a single Premier League championship.

Just how long a long shot were Leicester? They opened the year as a 5000-1 bet. Meaning, in case you don’t gamble, that if you bet $1 on Leicester to win the EPL on the first day of the season, you won $5,000 on this day in 2016. Fun fact: NO ONE bet on Leicester at 5,000-1. When the odds moved to 1,000-1, a man from Leicester bet $145. He won $145,000!!!

---

This is a free post. But, soon we will be putting up a paywall on much of the content here. Become a paid subscriber today to lock in the lowest possible rate: Just $5 a month or $50 for the year!

---

The previous season, Leicester was widely expected to be relegated — moved down a level in English soccer terms — as they were mired in the bottom 3 of the Premier League standings for almost the entire season. Only a late run of wins kept them in the league at all!

Here are the final standings from that year, with Leicester in 14th place:

As The Guardian wrote:

At the start of the season, bookmakers had Leicester at an incredible 5,000-1 to win the Premier League – greater than the odds on Kim Kardashian becoming the next US president. And yet it didn’t seem outlandish. Leicester’s best performance in their entire history was second place in 1928-29; in the Premier League era they’d never been higher than eighth. Last year, only a last-gasp escape from the relegation zone kept them in the top flight. Their history is one of a moderate provincial club, shorn of star names, bobbing between the first and second tier, eclipsed by their more famous East Midlands rivals Forest and Derby. Riyad Mahrez, their skinny-legged star who grew up in the northern Paris suburbs, admitted when he joined that he’d never even heard of Leicester City. “I thought they were a rugby club,” he said.

And yet, the Foxes won.

(Sidebar: In the wake of that win, Leicester fell on hard times. They were relegated down to the Championship — the 2nd league in England — in the 2022-2023 season. But, Leicester will return to the Premier League next year, earning promotion by winning the Championship this season.)

The remote odds set on Leicester at the start of the 2015-2016 season make them — from a gambling perspective — the longest shot to EVER win, the biggest upset in sports history.

But, there are a few other massive upsets that I think belong in that conversation. Below are a few of my nominees.

What did I miss?

• Buster Douglas knocks out Mike Tyson (1990)

I remember the run-up to this fight, which was in Tokyo. ALL of the coverage asked a simple question: How long would it take Tyson to knock out Douglas? Most people assumed that Iron Mike would dispatch the little-regarded Douglas after a round or two. No one thought that Douglas could win — much less knock out Tyson. Douglas, by the way, was a 42-1 betting underdog before the bout.

• U.S. men’s hockey team beats Russia (1980)

The “Miracle on Ice” is still the most famous hockey game ever played — even 40+ years after it happened. The Russian team was widely seen as unbeatable — they have won four gold medals — while the American team was comprised of a bunch of unknown amateurs. The U.S. won 4-3. Most people forget (or never knew) that this was not the gold-medal game. The Americans had to play Finland to win gold. They did — beating the Fins 3-2.

• New York Giants beat the New England Patriots in Super Bowl XLII (2008)

The Patriots were an unstoppable force in 2008, entering the season’s final game at 19-0. They were led by superstars like Tom Brady and Randy Moss. The Giants, on the other hand, had snuck into the playoffs as a wildcard team. The Patriots led all the way into the 4th quarter. But Giants QB Eli Manning led his team on a game-winning drive that was highlighted by David Tyree’s “helmet catch,” still one of the greatest grabs in football history.

• UMBC beats UVA in NCAA tournament (2018)

Entering this game, #16 seeds were 0-135 in the men’s NCAA Tournament. As in, no #1 seed had ever lost to a #16 seed. And no one thought University of Maryland Baltimore County would be the ones to make history. They had scraped into the tournament by winning the America East conference championship (and an automatic bid) in the game’s final seconds. But, they didn’t just beat Virginia. They crushed them -- by 20 points. And those letters suddenly stood for “U Might Be Cinderella.”

• Boris Becker wins Wimbledon (1985)

Becker is, obviously, a household name in tennis. But, he wasn’t back in 1985 when, a age 17(!), he became the youngest champion in the history of the tournament. Becker was unknown and unranked at the time. “It was such an extraordinary record that people looked at me like I was from Planet Mars,” Becker said years later. “They said I couldn’t have been human to do that. I get these looks, still, now.” Becker went on to win 5 more major championships — including two more Wimbledons. He remains in the news — for less, uh, stellar reasons.

• Rulon Gardner beats Alexander Karelin (2000)

Karelin was the most dominant force ever in Greco-Roman wrestling. He was unbeaten in international competitions — and had won three straight gold medals. (He had lost only one match ever — when he was a 19 year old in 1987!) He hadn’t been SCORED on in a decade. Gardner, on the other hand, had none of those accolades. He hadn’t won a college championship. Or, certainly, a world championship. But, in the gold medal match at the Sydney Olympics, Gardner beat Karelin 1-0. “When did I think I could beat him? About 10 minutes ago,” Gardner said right after the win. “I kept saying, ‘I think I can. I think I can.’ But it wasn't until it was over that I knew I could.” (Gardner’s life post-gold medal has been decidedly rocky.)