Manchester United Faces Stunning EFL Cup Exit Against Grimsby Town
Manchester United experienced a shocking early exit from the EFL Cup, losing to League Two side Grimsby Town in a penalty shootout, a result that is likely to be remembered for years.
The match ended 2-2 after United staged a comeback from a 2-0 deficit with just 15 minutes remaining, ultimately falling 12-11 in the penalty shootout.
This defeat is not the first notable upset United has faced in domestic cup competitions; a similar shock occurred 30 years ago when York City triumphed 3-0 at Old Trafford.
Following Grimsby's unexpected victory, BBC Sport highlights ten of the most significant upsets in both the FA Cup and EFL Cup history.
This list is not exhaustive, and readers are encouraged to share their thoughts in the comments, ranking the ten upsets and sharing their own experiences.
Grimsby 2-2 Manchester United (12-11 on penalties, League Cup, 2025)
The match was remarkable not only for the upset but also for its dramatic unfolding. Grimsby Town, a League Two team, managed to defeat top-flight Manchester United.
Grimsby took an early lead, going 2-0 up after 30 minutes with goals from Charles Vernam and Tyrell Warren. United responded with a goal from Bryan Mbeumo in the 75th minute, and Harry Maguire equalized in the 89th minute, forcing the match into penalties.
The penalty shootout was intense, with Clarke Oduor for Grimsby and Matheus Cunha for Manchester United being the only players to miss. After both teams had taken 11 penalties, Darragh Burns scored the decisive kick, and Mbeumo's second attempt struck the crossbar.
Plymouth 1-0 Liverpool (FA Cup, 2025)
In another upset, Liverpool made ten changes to their lineup after a recent EFL Cup semi-final victory, which cost them dearly. Plymouth was awarded a penalty shortly after halftime due to a handball by Harvey Elliott, and Ryan Hardie converted it emphatically.
Hardie nearly scored again soon after when his shot hit the post, but Plymouth held on for a historic victory, with goalkeeper Conor Hazard making crucial saves against a team that would go on to win the Premier League.
Chelsea 2-4 Bradford City (FA Cup, 2015)
Bradford City, ranked 49 places below Chelsea, pulled off a stunning upset at Stamford Bridge. Despite Chelsea establishing a 2-0 lead with goals from Gary Cahill and Ramires, Bradford fought back with goals from Jon Stead, Filipe Morais, and Andy Halliday to secure a remarkable victory.
Oldham 3-2 Liverpool (FA Cup, 2013)
In a memorable clash, Premier League side Liverpool, featuring stars like Luis Suarez and Raheem Sterling, faced a spirited Oldham team struggling with financial issues. Oldham took an early lead, and despite Liverpool's attempts to equalize, they ultimately succumbed to a 3-2 defeat.
Bradford City 1-1 Arsenal (3-2 on penalties, League Cup, 2012)
In the quarter-finals of the League Cup, Bradford City faced Arsenal as underdogs. After taking the lead through Garry Thompson, Bradford held on despite a late equalizer from Thomas Vermaelen, eventually winning the shootout 3-2.
Liverpool 2-2 Northampton (2-4 on penalties, League Cup, 2010)
Another surprising exit for Liverpool occurred at Anfield against Northampton. Despite initially taking the lead, Liverpool fell behind and were eliminated after a dramatic penalty shootout.
Manchester United 0-3 York City (League Cup, 1995)
Manchester United, under Sir Alex Ferguson, suffered a shocking defeat against York City at Old Trafford. Despite fielding a strong team, United was outplayed, culminating in a 3-0 loss.
Wrexham 2-1 Arsenal (FA Cup, 1992)
In a stunning upset, Wrexham, bottom of the Third Division, defeated reigning champions Arsenal. After being close to victory, Arsenal was stunned by two late goals from Wrexham.
Sutton 2-1 Coventry (FA Cup, 1989)
Sutton United achieved one of the biggest shocks in FA Cup history by defeating Coventry City, a team that had previously won the FA Cup. Matthew Hanlan's volleyed winner secured a memorable victory for the part-time club.
Hereford 2-1 Newcastle (FA Cup, 1972)
Newcastle United faced a shocking defeat against non-league Hereford United in the FA Cup. After a closely contested match, Hereford pulled off a dramatic victory.