Contact Us

Top 10 Biggest Upsets in Premier League History

In this blog post, we'll delve into the top 10 biggest upsets in Premier League history, celebrating the remarkable underdog triumphs that have left fans in awe.

Sourav Ghosh
Last updated: 19.10.2023
Top 10 Biggest Upsets in Premier League History

The Premier League, with its unpredictable nature and intense competition, has witnessed numerous shocking upsets over the years. While the league is renowned for its top clubs, these upsets are a reminder that football is full of surprises. In this blog post, we'll delve into the top 10 biggest upsets in Premier League history, celebrating the remarkable underdog triumphs that have left fans in awe.


1. Wimbledon vs Liverpool (1988)

The inaugural season of the Premier League kicked off with a major upset. Wimbledon, a club not particularly known for its footballing prowess, faced the mighty Liverpool. In a dramatic turn of events, Wimbledon secured a 2-1 victory, defying all odds. Vinnie Jones and Lawrie Sanchez became unlikely heroes for the Dons.


The match remains a testament to the unpredictable nature of football and the thrilling potential for lower-ranked teams to defeat giants.


2. Leicester City vs Manchester United (1998)


Manchester United, under the managerial reign of Sir Alex Ferguson, was an unstoppable force in the late 1990s. However, during the 1997-98 season, Leicester City, then a modest mid-table team, managed to shock the Red Devils. In a memorable match at Filbert Street, Leicester City emerged victorious with a 2-0 win. Tony Cottee and Matt Elliott etched their names in football history with their decisive goals.


3. Derby County vs Manchester United (1997)

Manchester United was dominating English football during the late 1990s, but Derby County, embroiled in a relegation battle, achieved the unthinkable. The Rams overcame the odds to defeat the Red Devils 3-2. Deon Burton, Francesco Baiano, and Paulo Wanchope were the heroes for Derby County in this thrilling encounter.


4. Leeds United vs Manchester United (2002)


In the 2001-2002 Premier League season, newly-promoted Leeds United faced off against their arch-rivals, Manchester United. The Red Devils were at the height of their powers, while Leeds had only just returned to the top flight. However, in a thrilling encounter, Leeds United pulled off a shocking 1-0 win at Elland Road. Mark Viduka scored the decisive goal, cementing his status as a Leeds legend.


This match was not just an upset but also a representation of the passionate rivalries that make football such an exhilarating sport. Leeds fans still cherish this victory as a symbol of their team's resilience against a footballing giant.


5. Blackpool vs Liverpool (2010)

Blackpool's journey in the 2010-11 Premier League season was a rollercoaster ride filled with surprises. One of the highlights of their campaign was a 2-1 victory over Liverpool at Bloomfield Road. What made this win even more special was the fact that Charlie Adam, who would later move to Liverpool, was one of the goal scorers for Blackpool.

6. Bournemouth vs Chelsea (2015)

In their debut Premier League season, Bournemouth faced a daunting challenge when reigning champions Chelsea visited Dean Court. The Cherries, unfazed by the opposition, stunned everyone with a 1-0 victory. Glenn Murray's goal was the difference-maker in this remarkable upset.


7. West Bromwich Albion vs Manchester United (2018)

Manchester United, under Jose Mourinho, was a formidable side in the 2017-18 season. However, West Bromwich Albion, struggling against relegation, delivered an unexpected blow to the title race. In April 2018, Jay Rodriguez scored the only goal of the match, securing a 1-0 victory for the Baggies.


This match ultimately handed the Premier League title to Manchester City, emphasizing how a single upset can have far-reaching consequences in the league.


8. Leicester City vs Manchester City (2020)


Leicester City's remarkable title-winning season in 2015-16 continues to be a source of inspiration for underdog teams. In February 2020, Leicester City faced the formidable Manchester City. Despite the odds, Leicester managed to secure a 1-0 victory, with Jamie Vardy finding the net. This result showcased Leicester's ability to remain competitive even against the league's heavyweights.


9. Swansea City vs Arsenal (2016)


Swansea City, then fighting against relegation, handed Arsenal a surprising 2-1 defeat in March 2016. This result had a significant impact on the title race that season. Goals from Wayne Routledge and Ashley Williams secured Swansea's victory.


The match exemplified how the Premier League can produce shock results that influence the title race.

10. West Ham United vs Manchester United (2007)

In May 2007, West Ham United, battling against relegation, faced Manchester United, who were challenging for the Premier League title. Despite being the underdogs, West Ham secured a memorable 1-0 victory. Carlos Tevez scored the winning goal, which ultimately played a role in West Ham's Premier League survival.




The Premier League, renowned for its competitiveness and surprises, has witnessed numerous upsets that continue to define the league's rich history. These victories by underdog teams, whether it's Wimbledon's historic win over Liverpool or Leicester City's improbable title-winning season, showcase the charm of football.


The Premier League is a unique platform where passion, determination, and teamwork can overcome the odds, and where underdog stories are celebrated by fans worldwide. These upsets are a testament to the captivating nature of the sport, where anything can happen on any given matchday. In the Premier League, the magic of football lies in its unpredictability, creating moments that keep fans on the edge of their seats and inspire hope and belief in the hearts of football enthusiasts.


Chase Your Sport

Stay up-to-date on the latest sports news, stats, expert analysis and trends, including cricket, football, wrestling, tennis, basketball, Formula One and more. Find previews, schedules, results of upcoming events, and fantasy tips on Chase Your Sport.