From Hereford to Grimsby: five major upsets in english football before arsenal’s league cup shock

Arsenal fall to Fleetwood

Fourth-tier Fleetwood Town stunned Arsenal in the League Cup fourth round on Tuesday. The Premier League champions drew 1-1 before losing 5-3 in the penalty shootout. The result was described as one of the greatest shocks in English football history. It also prompted a fresh comparison with other famous cup upsets.

Wrexham and Bradford triumph

In the previous season, 90 places separated Arsenal and Wrexham in the English Football League. Arsenal, managed by George Graham, had won their second title in three seasons, but Alan Smith’s goal was answered by Mickey Thomas’s free kick with 10 minutes left. Steve Watkin then scored a late winner.

Chelsea’s FA Cup success between 2006 and 2018 included five victories, but Jose Mourinho’s side lost at home to third-tier Bradford. After Gary Cahill and Ramires put the Premier League leaders 2-0 ahead, Jon Stead, Filipe Morais, Andy Halliday and Mark Yeates scored to complete Bradford’s comeback.

Hereford’s famous comeback

Hereford beat Newcastle 2-1 in the 1972 FA Cup. Malcolm Macdonald gave Newcastle the lead eight minutes from time, threatening to end the non-league team’s hopes. Ronnie Radford equalised with a 25-yard strike, and Ricky George scored the winner in extra time. The match also featured pitch invasions by fans wearing Parka coats.

Wimbledon defeat Liverpool

Wimbledon beat Liverpool 1-0 in the 1988 FA Cup final at Wembley. Liverpool had won the league title by nine points and were seeking a league and cup double, while Wimbledon had been in the third tier four years earlier.

Lawrie Sanchez headed in from a Dennis Wise free kick. Wimbledon goalkeeper Dave Beasant then saved John Aldridge’s penalty to secure the win.

Grimsby edge Manchester United

Grimsby beat Manchester United 12-11 on penalties in the 2025 League Cup. Charles Vernam and Tyrell Warren gave Grimsby a 2-0 lead in the second-round tie. Bryan Mbeumo and Harry Maguire brought United level to force extra time. Grimsby prevailed in the shootout, leaving United manager Ruben Amorim shell-shocked.