Five Epic Cup Shockers in Football History

Arsenal’s humiliating League Cup penalty shoot-out loss to fourth-tier Fleetwood joins an elite list of seismic English football upsets.

In the 1992 FA Cup, Wrexham stunned reigning champions Arsenal 2-1 after Mickey Thomas scored a late free kick and Steve Watkin netted an astonishing winner.

Decades later in 2015, third-tier Bradford overturned a two-goal deficit to defeat Premier League leaders Chelsea 4-2 at Stamford Bridge, scoring four unanswered goals to shatter Jose Mourinho’s side.

Non-league Hereford created another iconic moment in 1972 by knocking out Newcastle United 2-1, sealed by Ronnie Radford’s legendary 25-yard screamer and Ricky George’s extra-time winner.

In the 1988 FA Cup final, Wimbledon’s “Crazy Gang” defied all odds to defeat dominant league champions Liverpool 1-0.

Lawrie Sanchez scored the decisive header from Dennis Wise’s free-kick, while goalkeeper Dave Beasant made history by saving John Aldridge’s penalty to secure the trophy.

More recently, in the 2025 League Cup second round, fourth-tier Grimsby stunned Manchester United in a marathon penalty shoot-out.

After Grimsby took a 2-0 lead through Charles Vernam and Tyrell Warren, United fought back via Bryan Mbeumo and Harry Maguire to force extra time.

However, Grimsby held their nerve to win 12-11 on penalties, leaving United manager Ruben Amorim shell-shocked.