Football

10 biggest upsets in English cup competitions

Fleetwood Town’s penalty shootout victory over Arsenal has added another chapter to the history of major upsets in English football’s domestic cup competitions.

The League Two side beat the Premier League champions 5-3 on penalties after a 1-1 draw to reach the Carabao Cup quarter-finals, despite sitting 84 places below Arsenal in the English football pyramid.

Aaron Loupalo-Bi gave Fleetwood the lead in the 21st minute before Viktor Gyokeres equalised after the break. Arsenal’s task became more difficult when teenager Max Dowman was sent off in the 86th minute.

Fleetwood goalkeeper Jay Lynch saved Bruno Guimaraes’ penalty before Conor Haughey converted the decisive spot-kick to secure the club’s place in the last eight.

The result recalled several memorable occasions when lower-league sides eliminated established English football clubs from the FA Cup and League Cup.

Here are the 10 biggest upsets in English cup competitions.

1. Fleetwood Town 1-1 Arsenal (5-3 on penalties, Carabao Cup, 2026)

Fleetwood secured the biggest victory in the club’s history by eliminating Arsenal on penalties at Highbury Stadium.

The hosts took the lead through Loupalo-Bi before Gyokeres restored parity for Arsenal early in the second half.

Arsenal could not find a winner and were reduced to 10 men when Dowman was sent off late in the match. Lynch then saved Guimaraes’ penalty in the shootout, allowing Haughey to score the decisive kick and send Fleetwood into the quarter-finals for the first time.

2. Grimsby Town 2-2 Manchester United (12-11 on penalties, Carabao Cup, 2025)

Grimsby Town eliminated Manchester United in a dramatic penalty shootout after taking a two-goal lead against Ruben Amorim’s side.

Charles Vernam and Tyrell Warren scored in the opening 30 minutes to put the League Two hosts in control.

Bryan Mbeumo reduced the deficit with 15 minutes remaining before Harry Maguire equalised in the 89th minute to force extra time.

The tie was decided by a lengthy shootout in which both teams converted their first 11 penalties. Grimsby’s Darragh Burns scored to make it 12-11 before Mbeumo missed his second attempt, sending the League Two side through.

3. Chelsea 2-4 Bradford City (FA Cup, 2015)

Bradford City overturned a two-goal deficit to eliminate Chelsea at Stamford Bridge in the FA Cup fourth round.

Chelsea, who were leading the Premier League at the time, appeared in control after Gary Cahill and Ramires scored to give the hosts a 2-0 lead.

Bradford responded through Jon Stead before Filipe Morais equalised. Andy Halliday then put the League One side ahead, and Mark Yeates scored a fourth to complete the comeback against Jose Mourinho’s team.

The result remains one of the most memorable FA Cup upsets involving a lower-league club and a Premier League contender.

4. Oldham Athletic 3-2 Liverpool (FA Cup, 2013)

Oldham Athletic defeated Liverpool despite facing a team featuring several established Premier League players, including Luis Suarez, Raheem Sterling and Daniel Sturridge.

Matt Smith opened the scoring for the League One hosts with a header from a Youssouf M’Changama cross. Suarez equalised for Liverpool, but Smith capitalised on an error by goalkeeper Brad Jones to restore Oldham’s lead.

Reece Wabara added a third with a header at the back post, giving Oldham a 3-1 advantage. Joe Allen pulled one back for Liverpool, and manager Brendan Rodgers introduced Steven Gerrard in an attempt to rescue the tie.

Liverpool could not find another goal, and Oldham secured their place in the next round.

5. Bradford City 1-1 Arsenal (3-2 on penalties, League Cup, 2012)

Bradford City eliminated Arsenal in the League Cup quarter-finals after holding the Premier League side to a 1-1 draw and winning the penalty shootout 3-2.

Garry Thompson gave Bradford the lead with a volley before Arsenal equalised through Thomas Vermaelen, who headed in a cross from Santi Cazorla with two minutes of normal time remaining.

Arsenal failed to complete the comeback in extra time, leaving the tie to be decided from the spot.

Vermaelen missed his penalty in the shootout as Bradford secured a place in the semi-finals. The League Two side had already eliminated Wigan Athletic on penalties in the previous round.

6. Liverpool 2-2 Northampton Town (2-4 on penalties, League Cup, 2010)

Northampton Town defeated Liverpool on penalties at Anfield after a 2-2 draw in the League Cup.

Milan Jovanovic gave Liverpool the lead, but Billy McKay equalised for Northampton. Michael Jacobs then put the League Two side ahead early in extra time.

David Ngog scored a late equaliser to take the tie to penalties, where Northampton held their nerve to complete the upset.

ALSO READ: Fleetwood knock Arsenal out of Carabao Cup after penalty shootout

Abdul Osman converted the decisive spot-kick, sending Northampton through and handing Liverpool a disappointing home exit.

7. Manchester United 0-3 York City (League Cup, 1995)

York City recorded a memorable League Cup victory by beating Manchester United 3-0 at Old Trafford.

United manager Sir Alex Ferguson fielded a strong side that included David Beckham, Lee Sharpe and Ryan Giggs, but York took their chances against the Premier League club.

Paul Barnes scored twice for the visitors, including a penalty, before Tony Barras headed in a third goal.

Manchester United won the second leg 3-1 at Bootham Crescent, but York advanced 4-3 on aggregate after Scott Jordan scored the decisive goal.

8. Wrexham 2-1 Arsenal (FA Cup, 1992)

Wrexham produced one of the FA Cup’s most memorable upsets by beating reigning First Division champions Arsenal in the third round.

Arsenal appeared on course for victory after Alan Smith gave them the lead, but Wrexham fought back in the closing stages.

Mickey Thomas equalised with a free kick from about 25 yards before Steve Watkin scored the winner two minutes later.

The result sent Arsenal out of the competition against a Wrexham side that had finished 24th in the Fourth Division the previous season.

9. Sutton United 2-1 Coventry City (FA Cup, 1989)

Non-league Sutton United eliminated Coventry City, who had won the FA Cup in 1987, in one of the competition’s notable giant-killings.

Coventry arrived as the First Division side, while Sutton competed outside the Football League.

Matthew Hanlan scored the winning goal with a volley just before the hour mark, securing a 2-1 victory for Sutton and sending the non-league club through at the expense of their top-flight opponents.

10. Hereford United 2-1 Newcastle United (FA Cup, 1972)

Hereford United defeated top-flight Newcastle United after taking their FA Cup third-round tie to a replay.

The sides drew 2-2 at St James’ Park before meeting again at Edgar Street. Newcastle appeared set to progress when Malcolm Macdonald scored late in the replay.

Hereford responded through Ronnie Radford, whose long-range strike sent the match into extra time. Substitute Ricky George then scored the winner, completing the comeback and securing a place in FA Cup history for the non-league side.

Femi Akinyemi

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