Manchester United’s defeat to Grimsby Town in the EFL Cup will go down as one of the greatest humiliations in their history. But where does it rank among the most embarrassing cupsets from around Europe?
10. Real Unión 3-2 Real Madrid (Copa Del Rey 2008/09)
A Real Madrid team featuring Higuaín, Guti and Marcelo came unstuck against the third-tier Real Unión. Madrid won the return leg 4-3 but were still knocked out on away goals after the 6-6 aggregate draw. One of the darkest Copa nights in recent Los Blancos history.
9. PSG 1–2 Guingamp (Coupe de la Ligue, 2018/19)
Unbeaten at home in domestic cups for over 40 matches, PSG were in imperious form. The front three of Mbappe, Neymar and Di Maria were feared throughout Europe. Neymar put PSG ahead just after the hour mark, but two late penalties sealed a historic victory for Guingamp, having already missed one earlier in the game.
8. Oldham 3–2 Liverpool (FA Cup, 2012/13)
Luis Suarez, Raheem Sterling and Daniel Sturridge all started in what was expected to be an easy victory for Liverpool. The Premier League side couldn’t handle the physicality of Oldham’s Matt Smith who scored twice. Steven Gerrard was brought off the bench and came close to scoring, but Oldham held on to seal a famous FA Cup upset.
7. Wrexham 2–1 Arsenal (FA Cup, 1991/92)
Arsenal were the champions of England while Wrexham had finished bottom of the entire Football League the previous season. Alan Smith put Arsenal ahead, but a spirited comeback from the home side turned the game into one of the FA Cup’s most famous nights.
6. Man Utd 0–3 York City (League Cup, 1994/95)
Ferguson fielded a strong team with Giggs, Sharpe and Beckham all starting. York were second bottom of Division Two having only won two of their 10 matches that season. A Paul Barnes double set York up for a famous away victory. It was York’s finest hour and one of United’s worst.
5. Bradford City 4–2 Chelsea (FA Cup, 2014/15)
Chelsea, the Premier League champions, were 2-0 up within 40 minutes. Few could have expected what was to come. Bradford pulled one back before half time, but it wasn’t until the final fifteen minutes that the magic happened. Mourinho called the performance a “disgrace” – few would disagree.
4. Bradford City 1–1 Arsenal (3–2 pens, League Cup, 2011/12)
Bradford City pulled off one of the all-time greatest cup shocks when they beat Arsenal on penalties. Thomas Vermaelen had scored a late equaliser but went on to miss the decisive spot kick. The two sides were 65 places apart in the football pyramid before the clash. A true David vs Goliath moment.
3. Grimsby 2–2 Manchester United (12–11 pens, League Cup, 2025/26)
Losing to York in 1995 was bad, this was worse. Not only did a fourth tier side knock United out, they did so in dramatic fashion. Two goals down, United clawed back to force extra time, only to lose a marathon shootout when Bryan Mbeumo smashed his penalty against the bar. For sheer scale and circumstance, this ranks as one of United’s darkest nights.
2. Hereford United 2–1 Newcastle United (FA Cup, 1971/72)
The greatest upset in FA Cup history. Hereford United were a non-league team, plying their trade in the fifth tier of English football. Newcastle were a top division side but were no match on the day for the plucky underdogs. Ronnie Radford scored one of the most iconic goals in FA Cup history to equalise late on, before Ricky George scored the winner in extra time.
1. Alcorcón 4-0 Real Madrid (Copa del Rey 2009/10, 4–1 agg)
The benchmark for humiliation – The Alcorconazo.
Following a Champions League defeat to Milan and trailing Barcelona in La Liga, Pellegrini was keen to put out a strong side. The Madrid team featured Raúl, Guti and Benzema among others. Whilst it wasn’t a full strength Madrid side, nothing could excuse the capitulation that was to come.
Alcorcón were 3-0 up at half time before adding another in the second half. The minnows withstood a Madrid onslaught to secure the most infamous cup upset of all time.
Manchester United’s loss was bad – but nothing comes close to The Alcorconazo.
