The Most Iconic Moments in FA Cup History
The FA Cup is the oldest football competition in the world, and its history is packed with unforgettable moments of triumph, shock, and drama. From underdog victories to last-minute winners, the competition has delivered some of football’s most legendary scenes.
In this in-depth look, we explore the most iconic moments in Football association challenge cup history—those that have shaped the tournament, stunned the football world, and left an indelible mark on the sport.
1. The “Matthews Final” (1953) – A One-Man Masterclass
One of the greatest Football association challenge cup moments of all time, the 1953 final is forever remembered as “The Matthews Final”, named after Sir Stanley Matthews, who delivered a masterclass performance at 38 years old.
- The Match: Blackpool vs. Bolton Wanderers
- Key Moment: Blackpool trailed 3-1 before a stunning comeback, inspired by Matthews, who assisted the late winner in a 4-3 victory.
- Why It’s Iconic: It cemented Matthews’ place as one of football’s greatest-ever players and remains one of the most thrilling finals in Football association challenge cup history.
2. Sunderland’s Giant-Killing of Leeds United (1973)
A true underdog story, Sunderland, then a second-tier club, faced Leeds United, the reigning English champions, in the 1973 Football association challenge cup final.
- Key Moment: Goalkeeper Jim Montgomery pulled off a miraculous double save, denying Trevor Cherry and Peter Lorimer, to secure a 1-0 victory for Sunderland.
- Why It’s Iconic: It remains one of the greatest shocks in Football association challenge cup history, proving that the magic of the cup is alive and well.
3. Ricky Villa’s Solo Goal in the 1981 Final Replay
Tottenham Hotspur’s Ricky Villa scored one of the Football association challenge cup’s greatest goals in the 1981 final replay against Manchester City.
- Key Moment: Villa dribbled past four City defenders before slotting the ball past the goalkeeper in a 3-2 victory for Spurs.
- Why It’s Iconic: The goal is still considered one of the best ever scored in an Football association challenge cup final.
4. Wimbledon’s “Crazy Gang” Stun Liverpool (1988)
In another giant-killing moment, Wimbledon, nicknamed the “Crazy Gang”, shocked Liverpool, one of Europe’s best teams, in the 1988 FA Cup final.
- Key Moment: Lawrie Sanchez scored the game’s only goal, and goalkeeper Dave Beasant became the first to save a penalty in an FA Cup final, denying John Aldridge.
- Why It’s Iconic: A true underdog triumph against a dominant Liverpool side that had won the league.
5. The “Gerrard Final” (2006) – A Last-Minute Thunderbolt
The 2006 FA Cup final is often called “The Gerrard Final” because of Steven Gerrard’s heroic performance for Liverpool against West Ham.
- Key Moment: With Liverpool trailing 3-2 in the 91st minute, Gerrard unleashed a thunderous 35-yard strike, forcing extra time. Liverpool won on penalties.
- Why It’s Iconic: Gerrard’s last-minute heroics made this one of the greatest Football association challenge cup finals of all time.
6. Ryan Giggs’ Sensational Solo Goal vs. Arsenal (1999)
The 1999 FA Cup semi-final replay between Manchester United and Arsenal featured one of the most iconic goals in football history.
- Key Moment: Ryan Giggs picked up the ball in his own half, dribbled past four Arsenal defenders, and scored the winning goal in extra time.
- Why It’s Iconic: This moment helped Manchester United on their way to a historic treble-winning season.
7. Portsmouth’s Fairytale FA Cup Win (2008)
Portsmouth, an unfancied side, shocked the football world by winning the 2008 FA Cup, marking one of the greatest cup fairytales.
- Key Moment: Nwankwo Kanu’s goal secured a 1-0 victory over Cardiff City in the final.
- Why It’s Iconic: It was Portsmouth’s first major trophy in nearly 60 years, proving that the FA Cup could still deliver fairytale endings.
8. Wigan Athletic’s Incredible FA Cup Triumph (2013)
Wigan Athletic pulled off one of the biggest FA Cup upsets in history when they defeated Manchester City in the 2013 final.
- Key Moment: Ben Watson scored a last-minute header to win 1-0.
- Why It’s Iconic: Wigan became the first team to win the FA Cup and get relegated from the Premier League in the same season.
9. Leicester City’s First FA Cup Win (2021)
Despite their success in the Premier League, Leicester City had never won the FA Cup—until 2021, when they defeated Chelsea in the final.
- Key Moment: Youri Tielemans scored a stunning long-range goal to seal a 1-0 victory.
- Why It’s Iconic: Leicester finally lifted the FA Cup after losing four previous finals in their history.
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10. Manchester City’s Historic FA Cup Treble (2019 & 2023)
Manchester City dominated Watford 6-0 in the 2019 FA Cup final, equaling the biggest-ever win in a final. Then, in 2023, they won the FA Cup as part of their historic treble.
- Key Moment: Ilkay Gündogan’s record-breaking goal in the 2023 final—scoring just 12 seconds into the match against Manchester United.
- Why It’s Iconic: No English team had achieved a league, FA Cup, and Champions League treble since Manchester United in 1999.
Final Thoughts
The FA Cup continues to deliver unforgettable moments that remind us why it is one of the most beloved competitions in football. From shock upsets to stunning goals, these moments define the very essence of the tournament.
Which FA Cup moment do you think is the most iconic? Let us know in the comments!
