Top Five FA Cup Semifinal Upsets in History

The FA Cup is arguably the greatest cup game in the world, not just because of its age but also because of its limitless drama.

The competition is undoubtedly the oldest football competition in the world. It has been around for 153 years and has witnessed some significant fixtures. Drama should be expected, given that over 90,000 games have been played. Moreover, 142 finals have been played so far, and 44 different clubs have become champions after these contests.

And so the FA Cup holds a special place in football history.

Yet, among all the drama of the cup, the most entertaining events have come from the unlikely slaughter of big teams by 'smaller' clubs. 

Stories of non-league sides causing huge upsets by beating more established Premier League and Championship sides abound and form part of the stories of the FA Cup folklore. These dramas have certainly made FA Cup tickets a smart investment.

2023/24 Upsets

This season, we have witnessed some shocking results and upsets leading to the semifinals. From the third round, when Premier League teams joined the lower league sides in the competition, there have been several upsets, even though none of the lower league sides managed to beat a Premier League side at the initial stage. 

However, Championship side Leicester beat Premier League side Bournemouth in the fifth round, while Newcastle and Chelsea only managed to overcome Blackburn Rovers and Leeds United.

But after the fifth round, it became a Premier League affair except for one team that refused to give up. While every non-top-flight team ran out of gas, eventually, Coventry City refused to do so. The Sky Blues have made it to the semifinals in Wembley after beating Wolverhampton Wanderers in the quarterfinals. 

Wolves were the better side and were fancied to win. But Coventry went to the Molineux with belief and scored first before coming from 2-1 down to win it late in the game. What a game it was, and what a result for the 'small' club against their more flashy Premier League hosts.

Nevertheless, the Championship side is not the only team in the semifinals that beat a more fancied side in the last round. Manchester United's win against Liverpool in the quarterfinals was another upset, although not in the same proportion as Coventry's huge win over Wolves.

The Red Devils and Liverpool faced each other in the quarterfinals with differing forms. Liverpool, riding on the emotion from the announcement of Jürgen Klopp's departure at the end of the season, travelled to Old Trafford as the favourites after winning the Carabao Cup and brushing Sparta Praha aside to reach the last eight of the Europa League while being level on points with Arsenal at the top of the league table. In contrast, Man United were struggling after losing two in four games. 

But Erik ten Hag's side refused to bow to the Reds even when they were outplayed and toyed with sometimes at Old Trafford. They eventually found a way to beat Liverpool 4-3 in extra time, booking their place in the semifinals, where they will face the aforementioned Coventry City.

The other two teams in the last four, Chelsea and Manchester City, had tough draws in the last round but found a way to win. Chelsea didn't win without suffering, though, with the Blues throwing away a two-goal first-half lead before rallying late to beat Leicester City 4-2. However, City produced a professional performance against Newcastle to book their place in this round against Chelsea.

And now, ahead of Wembley's two great semifinal games, we look at the top five FA Cup semifinal upsets in the competition's history.

1. Portsmouth 2-0 Tottenham, 2010

Portsmouth's run to the 2010 FA Cup final was truly epic, not only because it was their second FA Cup final in three seasons but also because of the hurdles they had to surmount to reach the final.

Facing certain relegation in the 2009/10 season, reaching the FA Cup final was the last thing expected from Avram Grant's side. But despite their financial troubles, Portsmouth travelled to Wembley and conquered a more fancied Tottenham side coached by their former FA Cup-winning coach, Harry Redknapp. 

Although the game wasn't a classic in terms of quality, Portsmouth managed to hold Spurs to a goalless draw in normal time, thanks to the questionable playing surface. Extra time was where the real magic was born, with a goal from Frederic Piquionne and a Kevin Prince-Boateng penalty putting Portsmouth through to the final. 

However, the South Coast side eventually lost to Chelsea in the final, but their effort in the semifinals remains a fixture in FA Cup semifinal folklore.

2. Crystal Palace 4-3 Liverpool, 1990

In 1990, Liverpool was the best team in England by some distance and was expected to thrash lowly Crystal Palace when both sides met in the FA Cup semifinals. The Reds had already handed the Eagles a chastening 9-0 defeat earlier in the season, and nothing was expected to stop another rout in this FA Cup game.

But things went the other way for the Reds at Villa Park as Palace stunned Liverpool courtesy of a 109th goal by Palace midfielder Alan Pardew. The win denied Liverpool a double for the second consecutive season and booked Palace a place in the final against Man United. 

Unfortunately, the Eagles lost the two-legged final after an impressive fight in the first leg.

3. Tottenham 1-5 Chelsea (2012)

Although this wasn't the typical 'David versus Goliath' fight, yet it produced one of the most shocking results in FA Cup semifinal history.

Chelsea completely outclassed their London rivals in a game that may be remembered for a controversial call by referee Martin Atkinson. They scored four times in the second half to record one of the biggest scorelines in FA Cup semifinal history.

Guided by then-caretaker boss Roberto di Matteo, the Blues beat Liverpool in the final to win the trophy. Later that season, they also won the Champions League.

4. Middlesbrough 3-3 Chesterfield, 1997

Although Middlesbrough may not be playing in the top flight currently, there was a time when they were among the best teams in England.

In April 1997, Boro boasted one of English football's most talented teams, with Juninho, Emerson, and Fabrizio Ravanelli lining up for them. After overpowering Manchester City in the previous round, Bryan Robson's glamorous Middlesbrough faced third-tier Chesterfield at Old Trafford, sure of a win. This was a classic David versus Goliath case, and no one gave Chesterfield a chance.

But what followed was a truly epic 3-3 draw that Chesterfield could have even won if referee David Elleray had not ruled out Jonathan Howard's perfectly legitimate goal. Regardless, Chesterfield was proud of their effort even though they unfortunately lost the replay 3-0.

5. Wimbledon 2-1 Luton, 1988

Imagine Wrexham beating a good Newcastle side in the FA Cup semifinal in 2027. That's what it looked like when Wimbledon beat Luton Town in 1988. 

The Don's rise to the top of the English game is a fairytale that may never be repeated. In 1986, they were promoted to the First Division, just four seasons after being in the Fourth Division. Two seasons later, they went on an FA Cup run that led them to a meeting with First Division stalwarts Luton Town at White Hart Lane.  

A Dennis Wise winner took them to their first final against all odds, and the miracle continued in the final as they beat Liverpool in Wembley in one of the biggest upsets in FA Cup history. 

So should Coventry City beat Manchester United or Chelsea beat favourites and current holders Manchester City by a considerable scoreline in April, we could have another FA Cup semifinal classic to add to our list.