Fleetwood Town’s 1‑1 draw with Arsenal, decided by a 5‑3 penalty shoot‑out, sent the League Two club into the 2026 Carabao Cup quarter‑finals and shocked the Premier League champions. The match, played at Highbury Stadium, was one of the biggest upsets in the competition’s history, with Fleetwood ranked 84 places below Arsenal in the English football pyramid. The win has prompted BBC Sport to review some of the most memorable cup surprises across the FA Cup and League Cup.
The game began with Fleetwood’s Aaron Loupalo‑Bi scoring in the 21st minute, giving the fourth‑tier side an early advantage. Arsenal responded when Viktor Gyokeres levelled after the break, but the Gunners were reduced to ten men in the 86th minute when teenager Max Dowman was sent off following a challenge by Harrison Neal. In the ensuing penalty shoot‑out, Fleetwood’s goalkeeper Jay Lynch saved Bruno Guimaraes’ attempt before Conor Haughey converted the decisive spot‑kick, sparking celebrations among the players and the stands.
BBC Sport’s list of historic cup shocks includes other dramatic encounters. In 2025, Grimsby Town, also a League Two club, stunned Manchester United 2‑2 (12‑11 on pens) after taking a 2‑0 lead early in the match. Plymouth Argyle’s 1‑0 win over Liverpool in the 2025 FA Cup saw the Championship side hold on after a penalty from Ryan Hardie, while Bradford City’s 2‑4 victory over Chelsea in 2015 saw the 49‑place‑lower club defeat the Premier League leaders. Oldham’s 3‑2 win over Liverpool in 2013 and Bradford City’s 1‑1 draw with Arsenal (3‑2 on pens) in 2012 are also highlighted as significant upsets.
Other notable shocks include Liverpool’s 2‑2 draw with Northampton (2‑4 on pens) in the 2010 League Cup, Manchester United’s 0‑3 loss to York City in 1995, Wrexham’s 2‑1 win over Arsenal in the 1992 FA Cup, Sutton United’s 2‑1 victory against Coventry City in 1989, and Hereford United’s 2‑1 triumph over Newcastle in 1972. Each of these matches featured lower‑division or non‑league teams defeating top‑flight opposition in high‑stakes knockout fixtures.
With Fleetwood now in the quarter‑finals, the club will face a new challenge as they seek to build on this historic achievement. Their next opponent will be determined by the draw, but the result has already secured their place in the club’s record‑setting history and added another chapter to the long list of cup surprises that continue to captivate English football fans.