Ranking the five biggest financially lopsided defeats in English football: Man Utd top after Grimsby loss…
Manchester United’s shock defeat against Grimsby Town is the most financially lopsided defeat in English football history, but who else makes the top five?
To calculate this list, we’ve compared the squad value disparity between two sides and have found the five biggest occurrences of this phenomenon.
For context, Oldham’s victory against Everton in 2008 and Stevenage’s win against Newcastle in 2011 rank just outside the top five.
5. Tottenham vs Colchester (2019)
League Two Colchester Town dumped Tottenham out of the League Cup in September 2019, despite their squad being valued at 40 times less than their Premier League opponents.
The game finished goalless in regular time and Colchester managed to snatch the victory on penalties, winning 4-3.
“Colchester made a fantastic game, it was difficult. We are so disappointed we could not score in 90 minutes,” Spurs boss Mauricio Pochettino said after the game.
“They beat Palace on penalties too, that can happen. That’s the beauty of the competition, always something can happen.”
Pochettino never really recovered from the result and was sacked just a couple of months later.
4. Arsenal vs Wrexham (1992)
These days Wrexham’s squad is valued at around £41million, but that certainly wasn’t the case in 1992 when they beat Arsenal in the FA Cup third round.
From David Seaman and Tony Adams to Paul Merson and Ian Wright, Arsenal’s squad in 1991-92 was packed with superstars.
However, despite naming a strong starting XI, the Gunners were defeated by Wrexham thanks to late goals from Mickey Thomas and Steve Watkin.
At the time, Wrexham were in the fourth division and had a squad vlaue of around 60 times less than Arsenal.
3. Man City vs Wigan (2018)
During his time in England, Wigan Athletic are the only team that Pep Guardiola has a 100% loss record against.
Despite naming a full-strength XI, which featured the likes of Sergio Aguero, David Silva and Leroy Sane, Guardiola’s side still couldn’t find a way past Paul Cook’s men.
The momentum of the game switched on the stroke of half-time when Fabian Delph was shown a straight red card for a challenge on Wigan midfielder Max Power.
Wigan took advantage of their extra man in the second half as Will Grigg scored the winning goal in the 79th minute.
At the time of the game, Wigan had a squad worth 80 times less than Man City’s.
2. Chelsea vs Bradford (2015)
Jose Mourinho won the Premier League with Chelsea in 2014-15, but his side couldn’t get past Bradford in the FA Cup.
With the game taking place at Stamford Bridge and with Chelsea naming a strong XI, they were the overwhelming favourites going into the third-round tie.
However, Phil Parkinson’s side had other ideas and pulled off one of the shocks of the century, winning the game 4-2.
“I repeat a word I used before this match – It’s a disgrace for a big team to lose to a small team from a lower team,” Mourinho said after the match.
“Frustration is not the right word, embarrassed would be more appropriate.”
To put their disparity into context, Bradford’s squad was 240 times less valuable than Chelsea’s at the time.
1. Man Utd vs Grimsby (2025)
Ruben Amorim’s side have made history, but for all the wrong reasons.
The Portuguese boss was already under pressure after a lacklustre end to last season and United’s latest defeat against Grimsby could be the final nail in his coffin.
United found themselves two goals down at half-time, but late goals from Bryan Mbeumo and Harry Maguire offered a glimpse of hope.
After finishing 2-2, the game went to penalties and Grimsby pulled off one of their greatest ever results, beating the Red Devils 12-11 on spot kicks.
It’s the biggest ever financially lopsided defeat in English football history, with United’s squad being valued at 257 times more than Grimsby’s.
Amorim pulled no punches in his post-match interview and looked just as shellshocked as the fans in the stadium.
“I think the team and the players spoke really loud today, so that’s it,” Amorim said at full time.
“[Tonight] I think the best team won, the only team that was on the pitch.
“I think it’s really clear what they spoke, so let’s move on from this day. I think it was clear for everybody what happened today.
“The way we start the game without any intensity, we were completely lost.”
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