The Biggest Longshot Wins in Sports Betting History

In sports, traditionally, talent dictates outcomes. The better-skilled athletes or the better-composed teams usually win. However, there are instances where someone defies the odds, whether through superior preparation, implemented tactics, or just by having more will to win.

Triumphs that surpass expectations happen now and again in all athletic endeavors, as belief/grit can rewrite the script and win gamblers who sense these upsets coming hefty sums. Below, we get into four such examples: insurmountable challenges were overcome, and modest wagers morphed into life-changing payouts for some.

Leicester City’s Miracle EPL Title

Hardcore sports fans, especially those with a deep love for football, or soccer as it is called in the US, probably knew this unlikely event would claim the number one spot. Described by many as the most extraordinary sporting story ever, Leicester City’s five-thousand-to-one-odd stunning EPL 2015-16 season triumph is maybe the most improbable feat accomplished in any sport.

Someone beating a heavy favorite in one contest should not be massively shocking, as various unpredictable factors can sway the result in one game. Yet, winning a competition consisting of thirty-eight games spanning ten months requires a high level of consistency. Thus, it cannot be merely written off as a fluke.

Led by former Chelsea boss Claudio Ranieri, this modest club from the East Midlands, nicknamed The Foxes, had been pegged to find itself at the bottom of the table, struggling to avoid relegation, given that it finished in the fourteenth spot the previous season. No one believed they could go all the way, and bookmakers dismissed their chances, with some even giving them worse odds than a potential alien invasion. Still, such skepticism did not dissuade the Foxes, who lost only three matches under Ranieri’s stewardship and became a hope symbol for the underprivileged in the UK and the world, proving that teamwork and belief can sometimes beat teams put together by billions of pounds.

Greece Wins Euro 2004

Here is another football Cinderella story. In 2004, Portugal hosted the twelfth edition of the UEFA European Championship and was penciled in as one of the most likely teams to win this sixteen-team tournament. The Czech Republic, coming off a dominant qualification campaign, also looked like a killer side that may tear up its way to a first-place finish. France and Spain were powerhouses seen as sizeable front-runners for the Henri Delaunay Cup. However, what these four expected winners had in common was that they all went against the underestimated Greece and failed to defeat it. Spain was the only one that pulled out a draw, with France, the Czech Republic, and Portugal falling to it.

Portugal opened and closed the 2004 Euro with losses to Greece, in the first game of the competition and the final. Cristiano Ronaldo was expected to rise to superstar status in this tournament. But this phenomenon's dreams of attaining glory for his country were shattered by Greece, which was given one hundred-to-one odds to win the championship. Of the sixteen participating teams, only Latvia had worse winning chances. Bookmakers' odds did not discourage the compact squad coached by German Otto Rehhagel, who used a pragmatic defensive style that proved ruthlessly effective.

Greece has never come close to repeating its 2004 accomplishment, and it even failed to qualify for the 2006 World Cup. Still, its 2004 Euro run is the stuff of legend.

Buster Douglas TKOs Mike Tyson

Most veteran bettors are sure to agree that boxing is not one of the best sports to bet on, as dark horse victories always happen in combat sports. In MMA, more than in boxing, mixed martial arts is a more diverse type of competition, where competitors have more things to worry about, and there are more ways to lose.

That said, boxing has had its share of long-shot triumphs, as one miscalculation, and it all can be over. It only takes one good shot. A recent highly publicized shock win in pugilism was Andy Ruiz’s 2019 win over Anthony Joshua, where bookies had him as a twenty-five-to-one underdog.

Still, the most seismic underdog victory in boxing ever is, without question, James “Buster” Douglas TKO-ing Iron Mike Tyson in Tokyo’s Korakuen Hall in 1990. Tyson, the then-undefeated heavyweight champion, was a forty-two-to-one favorite and a cultural phenomenon. Most competitors saw him as a terrifying force of nature, boasting a thirty-seven-to-nil record.

After he dismantled Larry Holmes and Michael Spinks, likely no one but James Douglas thought he was the man to take away Tyson’s aura of invincibility, but that was what he did—bullying and outstriking Iron Mike up until the tenth round, when the fatigued Tyson fell to a ferocious four-punch combination from Douglas.

UMBC Conquers Virginia in NCAA March Madness

In March 2018, the University of Maryland, Baltimore County, did the unthinkable and beat the number one seed in the NCAA men’s basketball tournament as the sixteenth seed, marking the first time this has happened in history.

UMBC beat Virginia and crushed them with a twenty-point difference, 74–54, surmounting a forty-to-one probability, with a suffocating defense that Ryan Odom put in place that helped the Retrievers execute a college basketball win for the ages. It will get analyzed for decades to come.