Arsenal’s unexpected League Cup exit has revived memories of some of English football’s most remarkable giant-killing performances, when lower-league teams defied expectations to eliminate established clubs from major competitions.
The Gunners were beaten by fourth-tier Fleetwood on Tuesday, losing 5-3 in a penalty shootout after a 1-1 draw in their fourth-round encounter, in a result that added another chapter to the history of cup competitions producing unlikely winners.
The defeat recalls five other memorable upsets involving Arsenal, Chelsea, Newcastle United, Liverpool and Manchester United.
Wrexham 2 Arsenal 1 — 1992 FA Cup
Arsenal’s FA Cup defeat to Wrexham in 1992 remains one of the competition’s most celebrated shocks, given the considerable difference in stature between the two sides.
Arsenal had won the league title twice in three seasons under manager George Graham, while the gap between the clubs had stood at 90 places in the English Football League the previous season.
The north London side appeared on course to avoid an upset when Alan Smith gave them the lead, but Wrexham refused to surrender.
Mickey Thomas equalised with a free-kick in the closing 10 minutes before Steve Watkin scored a late winner to send the lower-league team through.
Chelsea 2 Bradford City 4 — 2015 FA Cup,,
Chelsea suffered a stunning reversal at Stamford Bridge in 2015 when third-tier Bradford City overturned a two-goal deficit to eliminate José Mourinho’s side from the FA Cup.
The Blues, who were leading the Premier League at the time, appeared firmly in control after goals from Gary Cahill and Ramires put them 2-0 ahead.
Bradford, however, mounted an extraordinary comeback, with Jon Stead, Filipe Morais, Andy Halliday and Mark Yeates finding the net to complete a 4-2 victory.
The result was particularly remarkable given Chelsea’s status among England’s leading clubs and their record of winning the FA Cup five times between 2006 and 2018.
Hereford United 2 Newcastle United 1 — 1972 FA Cup
Hereford United produced another famous FA Cup upset in 1972, defeating Newcastle United in a fourth-round tie remembered for dramatic scenes and a spectacular equaliser.
Newcastle appeared to have secured their progress when Malcolm Macdonald scored with eight minutes remaining, threatening to end the non-league side’s hopes of advancing.
But Hereford’s Ronnie Radford changed the contest with a powerful long-range strike from about 25 yards, widely remembered as one of the competition’s iconic goals.
Ricky George then scored in extra time to complete the comeback and secure a famous victory for Hereford.
Liverpool 0 Wimbledon 1 — 1988 FA Cup final
Wimbledon stunned Liverpool in the 1988 FA Cup final, denying the Merseyside club the chance to complete a league and cup double.
Liverpool entered the Wembley contest as overwhelming favourites after winning the league title by nine points, while Wimbledon had been playing in the third tier only four years earlier.
Wimbledon’s unconventional ‘Crazy Gang’ side, however, refused to be intimidated by their more decorated opponents.
Lawrie Sanchez scored the decisive goal with a header from Dennis Wise’s free-kick, while goalkeeper Dave Beasant preserved the lead by saving John Aldridge’s penalty.
The victory secured one of the most unexpected FA Cup final triumphs in English football.
Grimsby Town 2 Manchester United 2, Grimsby won 12-11 on penalties — 2025 League Cup
Grimsby Town delivered another major cup shock in 2025 when they eliminated Manchester United following a dramatic League Cup second-round encounter.
The lower-league side took a 2-0 lead through Charles Vernam and Tyrell Warren, exposing defensive weaknesses in their more illustrious opponents.
Manchester United fought back through Bryan Mbeumo and Harry Maguire, forcing the tie into extra time after recovering from the early setback.
Grimsby ultimately prevailed 12-11 in the penalty shootout, leaving then-United manager Ruben Amorim facing a damaging defeat.
The result reinforced the enduring unpredictability of English cup competitions, where a difference in league status and resources does not always determine the outcome.
