Top 10 all-time magical FA Cup matches

The Football Association Challenge Cup, more popularly known as the FA Cup, is the oldest football competition in domestic English football.

Since its inaugural edition, played in the 1871/72 season, the FA Cup has witnessed many memorable finals, incredible performances, and magical underdog moments that have lived in the hearts and minds of fans over the years. 

Here, we present our pick of the ten most magical FA Cup matches of all time. 

10. Wimbledon 1–0 Liverpool | 1988 FA Cup final

The Liverpool of the 1980s were a team no one fancied to play. Back then, the Reds were serial winners when it came to major silverware. They had just been crowned league champions, and a domestic double looked like a mere formality. However, Wimbledon had other plans going into this final at the old Wembley Stadium.

Liverpool and Wimbledon were both playing in the top flight, with 1987/88 being the latter’s second year in the First Division. The gulf in quality was still visible, however, as Liverpool had several high-quality players in their ranks that Wimbledon could not match on paper. Therefore, Liverpool were heavily tipped to win the FA Cup going into the final.

The match began with Liverpool dominating proceedings. For all their efforts, however, it was Wimbledon who took the lead in the 37th minute when Dennis Wise’s free kick was headed home by Lawrie Sanchez. Though Liverpool created many chances after that, Wimbledon keeper Dave Beasant stood like a wall between the opposition and his goal.

Liverpool were even awarded a penalty in the 60th minute for a foul on John Aldridge, and it looked like they would equalise and finally take the game away, but the ensuing shot from Aldridge was saved by a diving Beasant to keep his side’s lead intact. Wimbledon endured a lot of pressure from the Liverpool front line but ultimately managed to hold on to their slender lead to cause a massive upset. The Wimbledon players didn’t hide behind their limitations but fought for every ball, putting in crunching tackles and duels to ward off a far superior opposition and grab an unbelievable win.

This Wimbledon win was a prime example of why the FA Cup has been such a special tournament. Throughout its storied past, England’s oldest cup competition has repeatedly produced magical moments such as these, making it one of the most exciting cup competitions to watch.

9. Wigan Athletic 1–0 Manchester City | 2013 FA Cup final

The 2013 FA Cup final at the new Wembley was yet another incredible tale of an underdog side beating the odds to emerge victorious against a heavyweight opponent. 

In the 2012/13 season, Wigan and Manchester City were both playing in the Premier League, but the massive gulf in their positions made City the overwhelming favourites to win the FA Cup trophy here. City had already qualified for the UEFA Champions League before this game, which qualified Wigan Athletic for the UEFA Europa League after their semi-final win over Millwall. However, Wigan remained in danger of relegation from the English top flight. 

The first half ended goalless, with neither side able to break the deadlock. In the second half, Pablo Zabaleta was sent off for a second yellow-card offence, which made it even more difficult for City to attack. Ultimately, both teams ended regular time locked at 0–0.

In the first minute of stoppage-time, though, Wigan were awarded a corner kick, which was taken by Shaun Maloney. His cross was met by Ben Watson, who headed the ball into the net past City goalkeeper Joe Hart. This goal was enough to seal the cup for the Latics, much to the disbelief of thousands of both sets of fans at Wembley. 

Though Wigan couldn’t remain in the top flight that season and were relegated a few days later, they managed to end the season with major silverware and European qualification due to their heroics in the FA Cup. 

8. Wrexham 2–1 Arsenal | 1992 FA Cup 3rd round 

Another giant killing in the FA Cup arrived in 1992 in the third round. Arsenal were due to win the first division, while Welsh side Wrexham were on course to be relegated to the Football Conference. Hence, it was quite clear who the favourites were to cruise their way to the fourth round at a canter here. 

But we all know that football works in mysterious ways, and the same happened in this game. Watched by a sell-out crowd, Arsenal opened the scoring in the 43rd minute from a Paul Merson cross that was flicked into the box, with Alan Smith scoring the goal past Wrexham keeper Vince O’Keefe. Arsenal went into the break with a 1–0 lead. 

Wrexham came out with intent in the second half, denying Arsenal any time on the ball. They weren’t able to equalise until the 82nd minute, when Mickey Thomas scored from a sublime free kick past David Seaman into the top corner. Two minutes later, Wrexham scored the winner through Steve Watkin, who tapped the ball into the net from a Gordon Davies pass. Even though the Gunners dominated possession in the closing minutes, the Wrexham defence stood firm to hold on to the slender lead and knock the holders out of the FA Cup. 

This massive upset led to a pitch invasion by the Wrexham fans, who were delighted with their team’s unbelievable performance. Here was another match that encapsulated the magic of the Cup. 

7. Blackpool 4–3 Bolton Wanderers | 1953 FA Cup final

This game is popularly known as “the Matthews final”, named after Blackpool winger Stanley Matthews, whose performance was so unbelievable in this game that it even overshadowed his teammate Stan Mortensen’s hat-trick heroics.

Bolton Wanderers took the lead as early as the 75th second, with Nat Lofthouse scoring for the Trotters. Mortensen then equalised in the 35th minute. Four minutes later, Willie Moir reclaimed the lead for Bolton to make it 2–1.

In the 55th minute, Bolton increased their lead through Eric Bell, who was carrying an injury. With a 3–1 lead, everyone expected Bolton to see the game out comfortably, but, lo and behold, Stanley Matthews came to the party for Blackpool. He set up Mortensen with a perfect cross from the right wing to make it 3–2 in the 68th minute. Then, in the 89th minute, Mortensen scored from a wonderful free kick to restore parity and complete his hat-trick. In stoppage time, Matthews produced another perfect cross from the right, which Bill Perry converted for the Seasiders.

This was a fabulous performance from Matthews, who had lost two FA Cup finals before in 1948 and 1951 and took it upon himself to change his side’s fortunes. It was such a special win that even opposition player Nat Lofthouse applauded Blackpool’s heroics on the day.

6. Hereford 2–1 Newcastle United | 1972 FA Cup 3rd round 

This one is from the 1971/72 season, when non-League side Hereford got the better of top-flight outfit Newcastle United. This was another game that was considered to be a foregone conclusion, but Hereford put in an exceptional performance on their home ground to produce another huge upset in the FA Cup.

Playing in the FA Cup third round, the Magpies travelled to Edgar Street for the replay, having been held to a 2–2 draw at St James’ Park. At home, Newcastle conceded a quick goal as Brian Owen scored 17 seconds after kick-off — a dream start for Hereford. The hosts did go ahead with goals from Malcolm McDonald and John Tudor within 15 minutes, though they couldn’t keep hold of the lead as Hereford’s player-manager Collin Addison equalised with a long-range shot to take the tie to a replay.

At Edgar Street, both teams played well, but even after several chances none could score, with both goalkeepers making some fabulous saves. Newcastle did pile on more pressure in the second half, and with a header from McDonald off a Viv Busby cross they broke the deadlock in the 82nd minute. It felt like that strike would be enough to decide the tie, but Hereford’s Ronnie Radford produced a moment of magic three minutes later, unleashing a powerful 30-yard strike that flew into the top corner, thereby pushing the game into extra time. It was one of the best strikes in the FA Cup that season.

In extra time, substitute Ricky George provided the winner in the 103rd minute, stunning the Newcastle fans and sparking a pitch invasion after Hereford managed to hold on to the lead. This was the first time that a non-League side had beaten a team from the top division since Yeovil Town beat Sunderland in 1949, showcasing yet again that football games aren’t won on paper or by reputation, but by hard work, focus, and belief.

5. Shrewsbury Town 2–1 Everton | 2003 FA Cup 3rd round 

This was a third-round fixture between third-tier team Shrewsbury Town, who were up against Premier League regulars Everton at Gay Meadow. Given the gulf of quality between them, Everton were the hot favourites to progress to the fourth round, but the Shrews went on to tame the Toffees in another massive FA Cup upset.

It was Shrewsbury’s veteran striker Nigel Jemson who opened the scoring from an incredible free kick in the 38th minute to give the hosts a shock lead. However, Everton came back into the game at the hour mark, equalising through Swedish midfielder Niclas Alexandersson.

With both teams looking for a winner, it was Jemson again who popped up with an 89th minute header from a corner kick to give his side a historic win, knocking out a Premier League side that was placed 80 places above them in the English football pyramid.

Interestingly, Shrewsbury’s coach at the time was Kevin Ratcliffe, who had been Everton’s most successful captain during his playing days. It was probably written in the stars for Ratcliffe to knock out his former team of the competition, scripting a fabulous underdog story along the way.

4. Chelsea 2–4 Bradford City | 2015 FA Cup 4th round 

Chelsea were top of the Premier League table when they met sixth-placed League One side Bradford City in the fourth round of the FA Cup at Stamford Bridge in 2015. The Blues were the overwhelming favourites to progress to the next round and started the game in dominant fashion. Chelsea were 2–0 up by the 38th minute, with goals from centre-back Gary Cahill and midfielder Ramires. However, Bradford City’s striker Jon Stead pulled one back in the 41st minute to give his side some hope.

The second half proved to be the stuff of dreams, with the Bantams making a rousing comeback. In the 75th minute, winger Filipe Morais scored the equaliser. Bradford then stunned the Stamford Bridge crowd into silence as they took the lead in the 82nd minute through Andy Halliday, before killing the game in stoppage time as Mark Yeates added his name to the score sheet.

And so, Chelsea, who were certain to win the tie, were defeated by a team 49 places below them. Incidentally, this was also Chelsea’s first home loss of the season. Bradford City’s incredible comeback against top-flight table-toppers was another magical David versus Goliath fixture that warmed the hearts of all — another iconic moment etched into FA Cup lore.

3. West Ham United 3–3 Liverpool | 2006 FA Cup final

This was arguably one of the best finals contested in FA Cup history. The 2006 FA Cup final was played at the Millennium Stadium in Cardiff, with West Ham up against Liverpool, who were the favourites to win. But the beauty of this sport lies in the unpredictability it brings, surprising everyone with the twists and turns.

West Ham went 2–0 up courtesy of an own goal from Liverpool defender Jamie Carragher in the 21st minute and Dean Ashton in the 28th minute. Steven Gerrard rallied his team back by first setting up Djibril Cissé in the 32nd minute and then scoring the equaliser in the 54th minute.

With the match tied at 2–2, Paul Konchesky’s long cross at the far post was read wrongly by Pepe Reina, and the ball went into the top right corner, giving the Hammers the lead again. Liverpool struggled to find a response, and yet again it was their captain Gerrard who stepped up and equalised with a 30-yard screamer in stoppage time to push the game into extra time. The Englishman’s long-range effort remains one of the best goals ever scored in an FA Cup final.

The game ultimately went to penalties, where Liverpool keeper Pepe Reina turned hero by saving penalties from Bobby Zamora, Konchesky, and Anton Ferdinand. The Reds won the 2006 FA Cup final 3–1 on penalties.

Though there were quite a few heroes in that Liverpool team that night, none could be considered greater than their captain fantastic who, driven by his sheer single-mindedness to win the match for his team, made the most telling contribution. For that reason, this game is often fondly remembered as “the Gerrard final”. This was another one of those magical FA Cup matches that was exciting and had edge-of-the-seat action as well as a comeback of epic proportions.

2. Sutton United 2–1 Coventry City | 1989 FA Cup 3rd round 

Non-League club Sutton United had a memorable FA Cup campaign in 1989. They went on a rampage, defeating three Championship teams, including Leeds United. However, their biggest victims were Coventry City from the top flight, who had won the FA Cup two years before.

Playing away from home, Coventry were the overwhelming favourites going into this game due to the vast difference on paper in quality between the two teams, but as we all know, sometimes belief, focus, and intent can work wonders, which is exactly what happened in this game.

Sutton United took the lead in the 42nd minute when a curling corner kick by Mickey Stephens was volleyed in by Tony Rains. However, Coventry restored parity early in the second half, with David Phillips shooting past an advancing Bill Roffey. Sutton reclaimed the lead through another corner routine — this time a short one. In the 59th minute, Stephens passed to Phil Dawson, who put in an out-swinging cross that was struck in by Matthew Hanlan.

With several Coventry attempts at goal amounting to nothing, Sutton United managed to register a historic upset, defeating a top-tier side despite themselves being a non-League outfit. Sutton United were nowhere near Coventry City at the time, and even with a far inferior team the U’s added another chapter to the incredible legacy of the FA Cup by providing us with another surreal moment.

1. Macclesfield 2–1 Crystal Palace | 2026 FA Cup 3rd Round 

Sixth tier non-League side Macclesfield knocking out FA Cup holders Crystal Palace this year is a fairy tale that will be remembered for ages. The Eagles had held aloft the FA Cup trophy just eight months ago after defeating Manchester City in the final at Wembley, clinching their first major silverware with a fairy tale run of their own.

However, when it came to defending their title, the South London outfit ended up being stunned by a side 117 places below them in the English football pyramid, leading to arguably the most magical FA Cup moment ever. What makes this upset even more incredible is that this was the first time in more than a century when a non-League side sent the defending champions packing. It was in 1909 when Crystal Palace represented the non-League side of the equation and beat reigning FA Cup champions Wolves.

For a side employing teachers, candle makers, property developers, and footballers who did not succeed at club academies to defeat a top-flight team is beyond comprehension. It wasn’t a smash-and-grab performance, though; John Rooney’s team dominated Oliver Glasner’s Palace for the entire game. Their captain, Paul Dawson, put Macclesfield into the lead with a superbly placed header into the far corner two minutes before the break. The National League North side then doubled their advantage at the hour mark when Man City academy graduate Isaac Buckley-Ricketts’ improvised back heel ended up in the far corner. Even though Yeremy Pino pulled one back for the Eagles in the 90th minute, Macclesfield managed to hold on comfortably to record a historic FA Cup win.

What followed was a mix of disbelief and muted celebrations. For a club still reeling from the recent tragic loss of their 21-year-old player Ethan McLeod, this victory held a far deeper emotional meaning for the Macclesfield players and fans. Here, the Silkmen showed how, with belief and positive intent, even the impossible can be achieved.