Crystal Palace 4-3 Liverpool, 1990


Alan Pardew, for sure, would prefer to be remembered more for his contribution to this Crystal Palace classic than his David Brent impression on the Wembley touchline 26 years on.

In a topsy-turvy game, Palace – featuring current club ambassador Mark Bright – went ahead, but were forced to fight back against the soon-to-be Division One champions, Liverpool.

After an Ian Rush and John Barnes-inspired performance, Kenny Dlalglish’s side led 3-2, before an 88th-minute Palace equaliser took the game to extra time.

Cue Pardew.

The Eagles’ future boss headed in the winner to send his side through to a final that they agonisingly lost in a replay against Manchester United.

Liverpool, despite becoming the victim of a famous upset, went on to win the title, but this game was another signal that their dynasty was fading.

Tottenham Hotspur 3-1 Arsenal, 1991


This game was all about Gazza.

Inside 12 months of World Cup heartbreak at Italia ’90, Paul Gascoigne’s extraordinary 30-yard free kick was a reminder that he was still at home on the biggest stage.

Gascoigne, remarkably, wasn’t even fully fit for the game – he had just recovered from a hernia operation, and presumably may not have featured were he anybody else – but justified his selection.

Gary Lineker scored twice, sandwiching now-Sky Sports pundit Alan Smith’s goal, to send Spurs on their way to a final against Nottingham Forest that they also won.

But for Gascoigne, it was another case of slight disappointment. In the final, he injured himself after launching into a crazy sliding tackle and was unable to walk up the Wembley steps to receive his medal.

Chesterfield 3-3 Middlesbrough, 1997


While Chesterfield fans must largely remember this game fondly, it may be tinged with a hint of regret.

Two big refereeing decisions went against the Spireites – goal-line technology would have awarded them a goal that was not given, while a foul outside the penalty area was awarded as a Middlesbrough spot kick – leaving Boro with a sense of relief that they remained in the tie.

All of that despite the fact that third-tier Chesterfield – featuring Sean Dyche and Kevin Davies – equalised in the last minute of extra time to force a replay.

Having taken a 2-0 lead against their 10-man opponents, John Duncan’s side were blown away by the trickery of Juninho, who won a penalty amid a hugely influential individual display. 

Inspired by the Brazilian, Bryan Robson’s side fought back to lead 3-2 10 minutes into extra time.

But with Chesterfield’s final throw of the dice, Jamie Hewitt headed into the top corner to force an equaliser and replay.

Arsenal 1-2 Manchester United, 1999


A seminal chapter in the rapidly blossoming rivalry between Arsenal and Manchester United was written in arguably the FA Cup’s most famous match at Villa Park.

In the previous season – Arsene Wenger’s first full campaign in charge – Arsenal had both stolen the Premier League title and won the FA Cup, in doing so offering a threat to United’s dominance over English football.

Sir Alex Ferguson’s side, who tended not to take such threats all that well, were intent on revenge, and went some way to claiming it in this epic replay.

Level at 1-1 heading into the final quarter of an hour, Roy Keane’s red card swung the game in Arsenal’s favour, even more so when Ray Parlour earned his side an injury-time penalty.

Dennis Bergkamp’s effort was saved by Peter Schmeichel, though, sending the game to extra time and, memorably, prompting one of English football’s most iconic goals.

With the game petering out towards penalties, Ryan Giggs intercepted a wayward Patrick Vieira pass, weaved his way through a mesmerised Arsenal defence and slammed home, inspiring that celebration.

Wenger, who didn’t like losing much either, revealed afterwards that “the luckiest team won”.

Weeks later, the lucky United completed their unprecedented treble with Champions League final victory the Nou Camp.

Hull City 5-3 Sheffield United, 2014


Included in this list merely for the drama, rather than any particular narrative, this game is a new-Wembley classic.

Cup-specialists Sheffield United – who, despite League One status, reached the League Cup semi-finals the following season, too – led twice at Wembley, including 2-1 at half time.

But Premier League Hull never felt out of it, and their irresistible second-half comeback was too much for the Blades.

Matty Fryatt – who has made just 26 professional appearances since, and none since March 2015 – equalised five minutes into the second half.

And inside the next 20 minutes the Tigers led 4-2, through Tom Huddlestone and Stephen Quinn.

Nigel Clough’s side did not surrender, though, and got another goal back with just injury time to play.

But with bodies pushed forward, David Meyler broke away and slotted home to finish off a pulsating game, and send Hull into their first ever FA Cup final.

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