The Biggest FA Cup Upsets of All Time

The FA Cup has always held a special place in English football, prized for its long history and the possibility that the underdog might prevail against all expectations. Many famous teams have lifted the trophy, but some matches are remembered not for who won but for the shock of who lost. It’s iconic moments, such as whennon-leaguee sides defeat some of the clubs at the top of the English football pyramid, that truly make the FA Cup special. These dramatic results would have surprised not only fans but also those who had placed bets on the matches, with the shocks rippling across the wider gaming world, including casino-focused platforms like Lottomart Casino.

Macclesfield 2-1 Crystal Palace, 2026

In January 2026, potentially one of the biggest FA Cup upsets of all time occurred, seeing the current holders, Crystal Palace, defeated by non-league side Macclesfield 2-1 in the third round. Despite competing in the sixth tier, the club overcame the Premier League side who sat 117 places above them, thanks to a strong defensive display, earning a spot against Brentford in the 4th round. The victory captivated fans across the country, proving once again that in the FA Cup, ambition, belief, and determination can triumph over reputation, and that no result is ever certain.

Hereford United 2-1 Newcastle United, 1972

Hereford United’s 1972 victory over Newcastle United remains one of the most celebrated giant‑killings in FA Cup history. In the 3rd round replay, Ronnie Radford netted a stunning equaliser that has become iconic, which set up a memorable win for the non-league club. The home atmosphere was unlike any other, helping to push their squad to complete what is now regarded as one of the biggest underdog FA Cup stories. It is a moment that will forever live in the club’s history, as well as be remembered for many years by football fans across the country.

Wrexham 2-1 Arsenal, 1992

In the 1992 third round, Wrexham achieved what seemed impossible by defeating reigning league champions Arsenal. The Welsh club's Fourth Division side somehow managed to defy all expectations by managing to overcome a prolific Premier League Arsenal squad. The Racecourse Ground was packed and full of nervous fans as Wrexham managed to hold on thanks to some strong defensive work and a disciplined structure. Their victory demonstrated that league status offers no guarantee in knockout football and that part-time players can rise to extraordinary occasions.

Sutton United 2-1 Coventry City, 1989

Sutton United’s 2‑1 victory over Coventry City in 1989 remains one of the most talked-about FA Cup upsets. At a time when Coventry were established in the top flight, Sutton were a non-league side with little expectation of success. Yet they managed to triumph, inspiring fans and players alike. The match highlighted the classical magic of the FA Cup, showing how even the biggest of underdogs have the possibility of overcoming all odds. Cventry were left stunned by what was an incredibly complete and determined display from Sutton United.

Burnley 0-1 Lincoln City, 2017

Lincoln City’s 1‑0 victory over Burnley in the fifth round of the 2016–17 FA Cup provided one of the most thrilling modern upsets. The non-league side produced a dramatic late winner to knock out a Premier League opponent on their home ground, becoming the first team outside the Football League to reach the quarter-finals in over a century. The result captured the imagination of fans nationwide and reminded everyone that the FA Cup remains a competition where the underdog can defy all expectations.

Chelsea 2-4 Bradford City, 2016

In the 2014–15 FA Cup fourth round, Bradford City produced one of the most remarkable results of recent years by coming from two goals behind to beat Chelsea 4‑2 at Stamford Bridge. The League One side displayed incredible belief and attacking flair, leaving the Premier League champions stunned. It was a special performance from Bradford that knocked out one of the biggest clubs in the country in a fashion that could only occur in the FA Cup, proving that the lower league teams can very much compete against those in the top flight.

Wimbledon 1-0 Liverpool, 1988

The 1988 FA Cup final was one of the most incredible cup finals of all time, where the famous ‘Crazy Gang’ achieved one of the most remarkable victories in English football. Wimbledon managed to score the only goal at Wembley, beating a powerful Liverpool side, defying all odds despite not being the favourites. The victory is remembered not just for the scoreline but for the audacity of a small club overcoming one of the most celebrated teams of the era, and it remains an iconic moment in FA Cup folklore.

Wigan Athletic 1-0 Manchester City, 2013

In 2013, Wigan Athletic pulled off one of the most stunning FA Cup final upsets in modern football by defeating Manchester City 1‑0 at Wembley. Wigan were playing in the Premier League, yet few gave them much chance against Manchester City, who had been dominating English football. Despite that, Wigan produced a disciplined and resilient display, particularly in defence, which allowed them to hold firm and snatch a last-minute winner. The victory stunned fans across the country and perfectly illustrated the magic of the FA Cup, showing that determination and organisation can sometimes triumph over reputation and expectation.