Fleetwood Town's Shock Arsenal Victory Joins Pantheon of Cup Upsets

Fleetwood Town achieved the most significant victory in their history by defeating Arsenal on penalties to advance to the EFL Cup quarter-finals. The League Two club, ranked 84 places below their Premier League opponents, secured the improbable win at Highbury Stadium.

Aaron Loupalo-Bi gave Fleetwood a 21st-minute lead, which was later equalized by Viktor Gyokeres for Arsenal. The match took a dramatic turn when Arsenal's teenage player Max Dowman was sent off in the 86th minute. In the subsequent penalty shootout, Fleetwood goalkeeper Jay Lynch saved a crucial spot-kick, and Conor Haughey converted the winning penalty, igniting celebrations.

Notable Cup Upsets

Fleetwood's triumph prompts a reflection on some of the most surprising results in the FA Cup and League Cup.

In the 2025 League Cup, Grimsby Town, a League Two side, defeated Manchester United. Grimsby initially led 2-0, but Manchester United equalized late in the match. The shootout saw an extraordinary 12-11 scoreline, with Grimsby's Clarke Oduor scoring the decisive penalty after Manchester United's Matheus Cunha missed.

Also in 2025, Championship club Plymouth Argyle famously beat a heavily rotated Liverpool side 1-0 in the FA Cup. A penalty converted by Ryan Hardie proved to be the difference, with Plymouth goalkeeper Conor Hazard making key saves to preserve the lead against a Liverpool team that would go on to win the Premier League title.

The 2015 FA Cup saw Bradford City, then 49 places below Chelsea, overcome Jose Mourinho's Premier League leaders 4-2 at Stamford Bridge. After going down 2-0, Bradford scored four unanswered goals to secure a remarkable victory.

In 2013, Liverpool suffered another FA Cup upset when they lost 3-2 to League One side Oldham Athletic. Despite fielding a strong team, Liverpool could not overcome Oldham's spirited performance, which included two goals from Matt Smith.

The 2012 League Cup quarter-finals featured a significant shock when fourth-tier Bradford City held Premier League Arsenal to a 1-1 draw before winning 3-2 on penalties. Thomas Vermaelen missed the decisive penalty for Arsenal, mirroring the earlier miss by Manchester United's Matheus Cunha in their 2025 encounter.

Another Liverpool cup exit occurred in the 2010 League Cup when they were beaten on penalties by Northampton Town of League Two. After a 2-2 draw, Northampton secured a 4-2 victory in the shootout.

Manchester United experienced a humbling 3-0 defeat to York City in the 1995 League Cup. Despite fielding a strong lineup, United were comprehensively beaten, and a second-leg comeback was not enough to overturn the aggregate deficit.

In the 1992 FA Cup, Arsenal, the reigning Premiership champions, were defeated 2-1 by Third Division side Wrexham. Mickey Thomas's free-kick and Steve Watkin's late goal secured a famous win for Wrexham.

Sutton United, then a non-league side, recorded a 2-1 victory over top-flight Coventry City in the 1989 FA Cup. Matthew Hanlan scored the winning goal for Sutton.

One of the most iconic FA Cup upsets occurred in 1972 when non-league Hereford United defeated First Division Newcastle United 2-1 after a replay. Ronnie Radford's stunning long-range goal in extra time became legendary, with Ricky George scoring the winner.