Top 10 Shocking Cup Upsets in English Football

English football has seen some crazy moments where smaller clubs beat big teams in the FA Cup and League Cup.

From Hereford United beating Newcastle United to Bradford City’s amazing comeback against Chelsea, these games are unforgettable in English football.

Here are 10 of the most shocking cup upsets.

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

Hereford United made history by beating top team Newcastle United in a third-round replay of the FA Cup. Ronnie Radford scored an incredible long-range equaliser to take the game to extra time. Substitute Ricky George then scored the winning goal.

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

Wrexham, a team from the fourth division, shocked the reigning champions Arsenal. Alan Smith put Arsenal ahead, but Mickey Thomas equalised with a great free-kick. Steve Watkin then scored the winner, completing a fantastic comeback.

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

Sutton United, a non-league team, stunned Coventry City, who had won the FA Cup just two years before. Matthew Hanlan scored the winning goal, sending Sutton into football history.

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

Bradford City pulled off a remarkable comeback at Stamford Bridge after being 2-0 down to Chelsea. Goals from Jon Stead, Filipe Morais, Andy Halliday, and Mark Yeates turned things around, knocking out the Premier League leaders.

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

Bradford City, then in the fourth tier, took out Arsenal in the League Cup quarter-finals. Garry Thompson scored for Bradford, but Thomas Vermaelen equalised late on. Bradford won in the penalty shootout.

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

League One team Oldham Athletic shocked Liverpool, who had stars like Luis Suarez, Raheem Sterling, and Daniel Sturridge. Matt Smith scored twice, and Reece Wabara added another, securing a great win.

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

York City stunned Manchester United with a strong first-leg win at Old Trafford. Paul Barnes scored two goals and Tony Barras added a third. Even though United won the return leg, York advanced 4-3 on aggregate.

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

Northampton Town caused a big surprise at Anfield by holding Liverpool to a 2-2 draw. They then won the penalty shootout, showing great calm under pressure to eliminate a Premier League team.

1. Plymouth Argyle 1-0 Liverpool (FA Cup, 2025)

Plymouth Argyle knocked out Liverpool after Ryan Hardie scored a penalty in the second half. The Championship team defended well to take down a side that would later win the Premier League.

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

Grimsby Town shocked Manchester United by taking a 2-0 lead. United fought back, leading to penalties. After an incredible shootout, Grimsby won 12-11.

These memorable results show why the FA Cup and League Cup are so special. Smaller clubs can beat financial issues, league positions, and reputations to create unforgettable football moments.

From Hereford’s famous win in 1972 to recent shocks involving Arsenal, Chelsea, Liverpool, and Manchester United, English football shows that no team is guaranteed a win.