Arsenal Stunned by Fleetwood: What Are the Biggest Ever Cupsets?

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The magic of the cup has struck again, and this time it is Arsenal who have been left stunned.

Fleetwood Town, a fourth-tier club battling near the bottom of League Two, have knocked the Premier League champions out of the Carabao Cup after a dramatic penalty shootout victory.

Following a 1–1 draw, Fleetwood held their nerve to win 5–3 on penalties and book their place in the quarter-finals. It was a result few could have predicted before kick-off.

The result is particularly remarkable when you consider the gap between the two clubs. Arsenal operate at the very top of English football, while Fleetwood compete three divisions below them. The sides are 84 league places apart currently on the football pyramid.

But where does this result rank among the biggest cup upsets in English football history?

Macclesfield 2–1 Crystal Palace — 2026

Macclesfield's victory over Crystal Palace is one of the most extraordinary results in FA Cup history.

Macclesfield, competing in the sixth tier in the National League North, defeated the reigning FA Cup holders 2–1 in January 2026. Paul Dawson scored the opener before Isaac Buckley-Ricketts added a second, leaving Palace with too much to do despite a late free-kick from Yeremy Pino.

The Football Association described it as the greatest upset in FA Cup history, with the clubs separated by 117 league places. Macclesfield had also needed to navigate several qualifying rounds just to reach the main competition. Crystal Palace were also the holders at the time.

This is a useful benchmark for Arsenal's defeat to Fleetwood. Fleetwood are three divisions below Arsenal, but Macclesfield's position in non-league football meant Palace faced an even greater gap on the pyramid.

Wrexham 2–1 Arsenal — 1992

Arsenal's defeat to Fleetwood is not the first time the Gunners have suffered a famous cup humiliation.

In January 1992, Arsenal were reigning English champions and among the country's leading teams. Wrexham, meanwhile, were struggling in the fourth tier and had finished near the bottom of the Football League the previous season.

Alan Smith gave Arsenal the lead, and the Gunners looked set to progress. But Mickey Thomas scored a memorable free-kick before Steve Watkin struck the winner just two minutes later.

Wrexham's victory became one of the defining moments in FA Cup history. Contemporary retrospective accounts have put the gap between the clubs at around 90 league places.

The result is a reminder that even a club with Arsenal's history and resources can be caught out by a determined lower-league opponent.

Hereford United 2–1 Newcastle United — 1972

Hereford United's victory over Newcastle remains one of the most famous stories in the history of the FA Cup.

The non-league side had already earned a replay after drawing 2–2 with Newcastle at St James' Park. In the rematch, Newcastle looked on course to progress when Malcolm Macdonald scored late in normal time.

Then came Ronnie Radford's unforgettable long-range equaliser, which sent the tie into extra time. Ricky George subsequently scored the winner, completing one of English football's most celebrated giant-killings.

The historical pyramid is not directly identical to today's structure, but the significance is clear: Hereford were outside the Football League and defeated top-flight opposition.

Sutton United 2–1 Coventry City — 1989

Sutton United produced another famous FA Cup upset in 1989 when they eliminated Coventry City.

Coventry were playing in the First Division and had won the FA Cup only two years earlier. Sutton, by contrast, were a non-league club whose players were not operating at the same professional level as their opponents.

Sutton took the lead through Tony Raines before Coventry equalised. Matthew Hanlan then scored the winner to complete a famous victory for the part-time side.

It was a classic example of the FA Cup's ability to bring clubs from very different levels together and produce a result that nobody expected.

Shrewsbury Town 2–1 Everton — 2003

Shrewsbury Town's win over Everton is another outstanding example of a lower-league club overcoming a huge difference in status.

Everton were a Premier League side with ambitions of competing near the top end of the table. Shrewsbury were much further down the pyramid, but they produced an excellent performance to win 2–1.

Nigel Jemson scored both goals for Shrewsbury, including a superb free-kick. Everton had a young Wayne Rooney in their side, but the Premier League club could not avoid elimination. Retrospective accounts have placed the gap between the teams at around 80 league places.

Shrewsbury's victory shows why the gap between clubs should be considered alongside the result itself. It was not simply a lower-league team winning; it was a club from far down the pyramid beating established Premier League opposition.

The Carabao Cup has produced its own share of remarkable results. Unlike the FA Cup, it does not provide the same route for the lowest non-league clubs to face top-flight opponents, but the competition regularly pits Premier League sides against clubs from the Championship, League One and League Two.

Because the modern EFL Cup is largely a competition between Football League and Premier League clubs, a three-division gap is generally the biggest possible gap between participating clubs in the current structure.

Fleetwood Town 1–1 Arsenal — Fleetwood win 5–3 on penalties, 2026

Fleetwood's win deserves to sit near the top of any discussion of Carabao Cup giant-killings.

Arsenal are Premier League champions, while Fleetwood are in League Two. The fourth-tier club did not merely take the tie to penalties; they held their own against elite opposition and then converted every spot-kick to secure progression.

The 84-place gap between the clubs makes this a particularly striking result.

The shootout will be remembered for Fleetwood's composure, but the achievement goes beyond the penalties. The hosts had to stay in the contest for 90 minutes against a side with far greater resources and a squad full of high-level players.

Grimsby Town 2–2 Manchester United — Grimsby win 12–11 on penalties, 2025

Grimsby Town produced one of the most dramatic Carabao Cup upsets in recent memory when they eliminated Manchester United in August 2025.

The League Two side raced into a 2–0 lead before United fought back to draw 2–2. The tie went to a marathon penalty shootout, with Grimsby eventually winning 12–11.

Like Fleetwood, Grimsby were three divisions below their opponents. Their win was made even more remarkable by the way the match unfolded: United had time to recover from their poor start, but Grimsby ultimately prevailed.

The result is a useful comparison with Fleetwood's victory. Both underdogs came from League Two, both faced Premier League giants and both needed penalties to complete their shocks.

Bradford City 1–1 Arsenal — Bradford win 3–2 on penalties, 2012

Arsenal have now been involved in two of the most memorable Carabao Cup shocks against lower-league opposition.

In 2012, League Two Bradford City hosted Arsenal in the quarter-finals. Garry Thompson gave Bradford the lead, and although Thomas Vermaelen equalised late on, Arsenal could not finish the job in normal time.

Bradford won the shootout 3–2 and went on to reach the final, defeating Aston Villa in the semi-finals before losing to Swansea City at Wembley.

The result was especially significant because it was not an early-round tie against a heavily rotated side. Bradford eliminated Arsenal in the quarter-finals, when the prospect of reaching Wembley was very real.

Northampton Town 2–2 Liverpool — Northampton win 4–2 on penalties, 2010

Northampton Town's victory at Anfield was another remarkable Carabao Cup result.

Liverpool were one of England's biggest clubs, but League Two Northampton took them to extra time and penalties after a 2–2 draw. The Cobblers ultimately won the shootout 4–2 to progress.

Beating a major club away from home makes the result even more impressive. It is one thing for a lower-league side to take a Premier League team to penalties; it is another to do so at Anfield and emerge victorious.

MK Dons 4–0 Manchester United — 2014

MK Dons' 4–0 victory over Manchester United in 2014 was one of the most emphatic cup shocks of the modern era.

At the time, MK Dons were in League One and United were in the Premier League, leaving a two-division gap. The result was not a narrow penalty win either. MK Dons scored four times and knocked United out in convincing fashion.

While the pyramid gap was smaller than in Fleetwood's win, the scoreline made the result unforgettable. It demonstrated that a cup upset does not always need a late goal or a penalty shootout; sometimes the underdog can simply dominate.