Arsenal’s shock League Cup defeat to fourth-tier Fleetwood has revived memories of some of the most remarkable giant-killing acts in English football.
The Premier League champions were eliminated in the fourth round on Tuesday after a 1-1 draw was followed by a 5-3 penalty shootout defeat.
The result ranks among the competition’s biggest surprises and recalls several historic occasions when lower-league sides overcame more celebrated opponents.
Here are five memorable cup upsets.
Wrexham 2 Arsenal 1 — 1992 FA Cup
Arsenal entered the match as reigning English champions under manager George Graham, having won their second league title in three seasons. The gulf between the two teams was reflected in their league positions the previous season, when they had been separated by 90 places.
Alan Smith gave Arsenal the lead, but Wrexham fought back when Mickey Thomas scored from a free-kick with 10 minutes remaining. Steve Watkin then struck a late winner to complete a stunning victory.
Chelsea 2 Bradford City 4 — 2015 FA Cup
Chelsea suffered a painful home defeat against third-tier Bradford City despite taking a two-goal lead at Stamford Bridge.
Gary Cahill and Ramires scored for Jose Mourinho’s side, putting the Premier League leaders in a seemingly comfortable position.
Bradford responded with goals from Jon Stead, Filipe Morais, Andy Halliday and Mark Yeates to secure an extraordinary comeback and eliminate the favourites.
Hereford United 2 Newcastle United 1 — 1972 FA Cup
Hereford United produced one of the competition’s most famous upsets in a fourth-round encounter featuring dramatic late goals and jubilant pitch invasions.
Newcastle appeared to be heading towards victory when Malcolm Macdonald scored with eight minutes remaining.
However, Hereford’s Ronnie Radford equalised with a powerful effort from approximately 25 yards, one of the FA Cup’s most celebrated goals. Ricky George then scored in extra time to give the non-league side a memorable win.
Liverpool 0 Wimbledon 1 — 1988 FA Cup
Wimbledon stunned Liverpool in the FA Cup final at Wembley, denying the Merseyside club a league and cup double.
Liverpool were widely expected to win after securing the league title by nine points, while Wimbledon had been playing in the third tier only four years earlier.
Wimbledon’s Lawrie Sanchez scored with a header from a Dennis Wise free-kick. Goalkeeper Dave Beasant then saved a penalty from John Aldridge to preserve the lead and seal the club’s historic triumph.
Grimsby Town 2 Manchester United 2 — Grimsby won 12-11 on penalties, 2025 League Cup
Grimsby Town delivered another memorable upset when they eliminated Manchester United in the second round of the League Cup in 2025.
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 responded through Bryan Mbeumo and Harry Maguire to force extra time. However, Grimsby prevailed in a dramatic penalty shootout, winning 12-11 and leaving then-manager Ruben Amorim facing a humiliating early cup exit.
These results demonstrate how domestic cup competitions can provide lower-league clubs with opportunities to challenge established football powers and produce some of the sport’s most memorable moments.
Source: Vanguard
