Premier League champions Arsenal suffered a stunning League Cup fourth-round defeat, losing 5-3 on penalties to fourth-tier Fleetwood Town after a 1-1 draw. This upset is considered one of English football's greatest shocks. The article highlights five other historic cup upsets. In the 1992 FA Cup, Wrexham famously beat Arsenal 2-1, with Mickey Thomas and Steve Watkin scoring against George Graham's side. Chelsea, then Premier League leaders, were humbled 4-2 by third-tier Bradford in the 2015 FA Cup, despite goals from Gary Cahill and Ramires. Hereford defeated Newcastle 2-1 in the 1972 FA Cup, with Ronnie Radford and Ricky George securing the win. The 1988 FA Cup final saw Wimbledon's 'Crazy Gang' beat Liverpool 1-0, thanks to Lawrie Sanchez's header and Dave Beasant's penalty save from John Aldridge. Finally, Grimsby defeated Manchester United 12-11 on penalties in the 2025 League Cup, leaving manager Ruben Amorim shell-shocked.