Fleetwood Town has secured a place in the League Cup quarter-finals for the first time following a dramatic victory over Arsenal at Highbury Stadium. The League Two side, currently sitting 19th in the fourth tier of English football, pulled off one of the competition’s greatest upsets by defeating the Premier League champions 5-3 on penalties after a 1-1 draw. And you can leave your thoughts in the comments, rank the historic upsets and share your results, this isn’t an exhaustive list. Fleetwood 1-1 Arsenal (5-3 on pens, League Cup, 2026).
The visitors initially faced a deficit when Aaron Loupalo-Bi netted a 21st-minute opener for the hosts.
Although Viktor Gyokeres equalized for Arsenal after the break, the London club struggled to capitalize on their momentum. Their situation worsened in the 86th minute when teenager Max Dowman was dismissed for kicking out during a challenge by Harrison Neal. The match was ultimately decided in the shootout, where Fleetwood goalkeeper Jay Lynch saved a spot-kick from Bruno Guimaraes, allowing Conor Haughey to convert the decisive penalty.
This historic result against an opponent ranked 84 places higher in the football pyramid recalls several iconic cup shocks from the past.
In 2025, Grimsby Town achieved an astonishing 2-2 draw with Manchester United before winning 12-11 on penalties. An upset as astonishing for its manner as it was for its proportions. With Clarke Oduor for Grimsby and Matheus Cunha for Manchester United missing the only penalties as each side’s 11 took one, but an incredible shootout followed.
Grimsby had established a 2-0 lead within 30 minutes through goals from Charles Vernam and Tyrell Warren, before Manchester United clawed their way back with late goals from Bryan Mbeumo and Harry Maguire. The visitors pulled one back through Bryan Mbeumo with 15 minutes to go and United looked like they might squeeze through when Harry Maguire went on to level in the 89th minute.
The subsequent marathon shootout saw both sides use all 11 players before Mbeumo eventually struck the crossbar.
Another notable upset occurred in 2025 when a Championship side, Plymouth Argyle, defeated Liverpool 1-0 in the FA Cup. Despite Liverpool manager Arne Slot making 10 changes to his squad, Plymouth held firm after Ryan Hardie converted a second-half penalty awarded for a handball by Harvey Elliott. Conor Hazard produced vital late saves to secure the win for the bottom-placed Championship team. Arne Slot made 10 changes to his Liverpool side after they had won an EFL Cup semi-final in their previous game and the Reds were made to pay. Hardie almost added a second shortly afterwards when his shot was turned on to the post by Liverpool keeper Caoimhin Kelleher.
Historical shocks in the FA Cup include Bradford City’s 4-2 victory over Chelsea in 2015. Despite trailing 2-0 early on, the League One side fought back through Jon Stead and Filipe Morais, with Andy Halliday and Mark Yeats later sealing a remarkable comeback. Similarly, Oldham Athletic’s 3-2 win against a star-studded Liverpool team in 2013 remains a standout, defined by Matt Smith’s two goals and Reece Wabara’s late header, which outweighed efforts from Luis Suarez and Joe Allen. Who at that point were top of the Premier League, bradford ranked 49 places below their opponents as they travelled to Stamford Bridge to take on Chelsea. Gary Cahill and Ramires netted to put the hosts 2-0 up and give Chelsea firm control of the fourth-round tie. With the likes of Luis Suarez, Raheem Sterling and Daniel Sturridge all starting, premier League giants Liverpool had ample strength at Boundary Park. With Matt Smith nodding in a Youssouf M’Changama cross to open the scoring, league One hosts Oldham were in the midst of financial problems but produced a spirited display against the odds. But it was not enough to avoid defeat, joe Allen volleyed home to pull one back and Liverpool brought on Steven Gerrard.
In the League Cup, Bradford City previously eliminated Arsenal in 2012 by winning 3-2 on penalties following a 1-1 draw. Garry Thompson opened the scoring for the fourth-tier side before Thomas Vermaelen’s late equalizer set the stage for the dramatic shootout. In 2010, Northampton Town similarly knocked Liverpool out of the League Cup at Anfield, winning 4-2 on penalties after Michael Jacobs’ extra-time goal gave the Cobblers a brief lead before David Ngog forced a late reply. Up for a fight at home to Arsene Wenger’s Gunners, Garry Thompson volleyed the Bantams ahead before Thomas Vermaelen headed home a Santi Cazorla cross with just two minutes of normal time remaining. Beating three EFL teams – including Leeds United – before losing to Arsenal in the fifth round, sutton United had a memorable cup run in 2016-17.
Further back, the 1995 League Cup saw York City defeat a Manchester United squad featuring David Beckham and Ryan Giggs, winning 3-0 at Old Trafford with two goals from Paul Barnes. Although United won the return leg, York advanced 4-3 on aggregate. Finally, the 1992 FA Cup witnessed Wrexham—then 24th in the Third Division—defeat the reigning league champions Arsenal 2-1, thanks to a iconic 25-yard free kick from Mickey Thomas and a decisive strike by Steve Watkin. Ruben Amorim is not the first Manchester United to suffer a shock in the League Cup – even Sir Alex Ferguson has faced the same.
The legendary 1972 FA Cup clash between non-league Hereford United and top-flight Newcastle remains perhaps the most famous upset of all. After forcing a replay, Hereford trailed to a late goal by Malcolm McDonald before Ronnie Radford scored a spectacular 30-yard effort to force extra time. Substitute Ricky George then scored the winner, marking the first time a non-league club had ousted a First Division side since 1949. The non-league side took on a Coventry team who were then in the First Division and had won the FA Cup in 1987. However, the non-leaguers had other ideas and Ronnie Radford popped up to score the most famous 30-yard goal in FA Cup history to take the game into extra time.
