Eighty-four places separated Fleetwood Town and Arsenal in the English pyramid as the two sides met in the League Cup fourth round in October 2026. Somewhat fittingly, at Fleetwood’s Highbury — the one on the Fylde coast — that gap counted for nothing, and the League Two side knocked out the reigning Premier League champions on penalties.
That is the league cup’s enduring charm: big clubs treat it as a squad competition; smaller ones treat it as a cup final. Since the League Cup’s creation in 1960, that mismatch in motivation has produced some of English football’s most famous nights. Here are 15 of the biggest, ranked by the size of the shock.
15
Chelsea 1-1 Burnley (4-5P) – 2008, fourth round
Championship Burnley held Luiz Felipe Scolari’s Chelsea at Stamford Bridge and then won the shootout, with goalkeeper Brian Jensen the hero. Owen Coyle’s team were not finished: they beat Arsenal 2-0 in the quarter-final and came within minutes of Wembley, before Tottenham scored twice late in extra time of the semi-final second leg.
14
Bristol City 2-1 Manchester United – 2017, quarter-final
José Mourinho were the holders of the League Cup at the time and fielded a side containing Paul Pogba and Zlatan Ibrahimović, yet the Championship’s Bristol City deserved their win at Ashton Gate. Joe Bryan opened the scoring, Ibrahimović, one of the greatest football players of all time, equalised, and Korey Smith drilled a stoppage-time winner. Lee Johnson’s side had already beaten Watford, Stoke and Crystal Palace, and went on to run Manchester City close in the semi-final.
13
Liverpool 1-2 Grimsby Town (AET) – 2001, third round
Liverpool were the holders, fresh from a cup treble, when second-tier Grimsby visited Anfield. Gerard Houllier fielded a much-changed side, but it still contained plenty of first-team experience. Grimsby took the tie to extra time and Phil Jevons settled it with a spectacular long-range strike, leaving the holders out at the first hurdle of their defense.
12
Liverpool 2-2 Northampton Town (2-4P) – 2010, third round
Roy Hodgson’s troubled Liverpool reign produced few lower moments than when Northampton went to Anfield. The League Two side matched their hosts over 120 minutes and held their nerve in the shootout. Liverpool had picked a young side, but one with experienced names in it, and the result deepened the gloom around Hodgson, who was gone within four months.
11
Sheffield Wednesday 1-0 Manchester United – 1991 final
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Ron Atkinson’s Second Division Wednesday faced the club that had sacked him in 1986. John Sheridan’s first-half strike settled it, and Wednesday sealed promotion weeks later. United went on to win the Cup Winners’ Cup that spring, which only made the Wembley defeat look all the more surprising. Wednesday remain the last club from outside the top flight to lift the League Cup trophy.
10
Colchester United 0-0 Tottenham (4-3P) – 2019, third round
Four months after facing Liverpool in the Champions League final, Spurs found themselves knocked out of the League Cup by a League Two side in Colchester. Mauricio Pochettino’s team could not break down a disciplined Colchester, and Christian Eriksen and Lucas Moura both missed in the shootout. It was a symptom of a club in decline and, sure enough, Pochettino was sacked less than two months later.
9
Grimsby Town 2-2 Manchester United (12-11P) – 2025, second round
Ruben Amorim’s United went to Blundell Park and fell 2-0 behind to League Two Grimsby within half an hour, through Charles Vernam and Tyrell Warren. Bryan Mbeumo and Harry Maguire forced a shootout, which lasted 26 kicks until the former struck the bar to coronate one of the most chaotic nights in the competition’s history.
8
Bradford City 4-3 Aston Villa (agg) – 2013, semi-final
Bradford proved that their victory over Arsenal in the previous round was no accident as they beat Premier League Villa 3-1 at Valley Parade, before only losing 2-1 at Villa Park. James Hanson’s header proved decisive as the Bantams became the first fourth-tier side to reach the final since Rochdale in 1962. Swansea beat them 5-0 in the final, but the run remains the gold standard for League Cup giant-killing.
7
MK Dons 4-0 Manchester United – 2014, second round
Louis van Gaal’s first season as Manchester United boss began with humiliation as League One MK Dons dismantled a Red Devils side that still contained several internationals, with Will Grigg and Benik Afobe scoring twice each. Barely a year after United’s last league title, the scoreline became a symbol of the turmoil of the post-Ferguson era.
6
Manchester United 3-4 York City (agg) – 1995, second round
Alex Ferguson’s United, months from completing the double, rested senior players for a first leg against third-tier York. They paid heavily as York won 3-0 at Old Trafford, with Paul Barnes scoring twice. United won the second leg 3-1 at Bootham Crescent with a far stronger side, but York went through 4-3 on aggregate, one of Ferguson’s most embarrassing evenings.
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