10 biggest upsets in the League cup

The League Cup first round takes place this weekend and while the competition is not as coveted as the FA Cup, it still provides an excellent showcase for the EFL and provides a route into Europe for the winner.

The current holders of the competition are Manchester City, who beat Arsenal at Wembley back in March thanks to a brace from Nico O'Reilly.

Ahead of the first round this weekend, we have compiled the 10 biggest upsets of the League Cup.

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The most recent fixture on this list took place last season, in one of the most damaging results in the ill-fated reign of Ruben Amorim at Manchester United.

Three months prior, his Manchester United suffered the ignominy of losing a European final to Tottenham Hotspur following their worst finish in Premier League history. Fast forward to August and Manchester United found themselves in the second round of the League Cup for the first time since 2014, where they were beaten by MK Dons under Louis van Gaal.

The Red Devils had spent big in the summer, acquiring Matheus Cunha, Bryan Mbeumo and Benjamin Sesko and an opportunity to win a trophy that season was there, but as we know in football, nothing is guaranteed.

Ruben Amorim's 3-4-2-1, which had been heavily criticised during his reign at the club, was exploited by an excellent showing from Grimsby Town as the Mariners raced into a two-goal lead inside the first 30 minutes. Throughout the course of the game, the Red Devils were on the ropes and yet through Bryan Mbeumo and Harry Maguire they dragged the tie to penalties.

Fate favoured the Mariners, however, with Mbeumo missing the decisive penalty to send Grimsby fans into wild celebrations, while Ruben Amorim stared at the tactics board.

The 2022/23 season will be fondly remembered by Manchester City as the season in which they matched their city rivals Manchester United in becoming the second English team to win the recognised treble of the Premier League, the FA Cup and the Champions League.

However, what gets forgotten is how close they could have realistically come to completing the unprecedented quadruple but unfortunately for them, Nathan Jones' Southampton side stood in their way.

Now, Southampton have not enjoyed their last two seasons in the top flight by any means, but the odd result here and there, including this one against Manchester City, provided a shining light for the Saints.

Manchester City fielded a rotated yet strong eleven fielding the likes of Jack Grealish, Kyle Walker, Phil Foden and Julian Alvarez but were stunned on that night thanks to goals from Moussa Djenepo and Sekou Mara.

Speaking of MK Dons, Louis Van Gaal’s first competitive match as manager of Manchester United where he got off to the worst possible start after losing 4-0 away to League 2 side MK Dons during the 14/15 season. 2 goals each from Will Grigg and Benik Afobe sealed the embarrassing exit for Manchester United. A young Dele Alli also made an appearance for MK Dons in the match which definitely would have increased the interest in the young midfielder.

Despite not possessing the quality that had under Rafa Benitez and currently have under Jurgen Klopp, the visit of League 2 Northampton Town to Anfield back in 2010 seemed like it would be an easy victory for Liverpool and an early goal from Milan Jovanovic made it look like it would be. However, a Billy McKay equaliser took the game to extra time where a late goal from David N’Gog cancelled out Michael Jacob’s goal to take the game to penalties with Northampton winning 2-4.

It’s incredible how many bets were ruined on Tuesday evening thanks to Tottenham’s shocking loss to League 2 side Colchester United. Tottenham didn’t go into the game in the best form having won only 1 of their previous 6 games in all competitions, but a trip to League 2 Colchester seemed like an easy opportunity for Spurs to advance to the next round. After finishing goalless the game went to penalties, with misses from Christian Eriksen and Lucas Moura knocking Spurs out of the League Cup and giving Colchester a famous victory.

Arsenal were in a difficult period following the relocation to the Emirates Stadium, whilst they maintained an excellent record of Champions League qualification, the Gunners were on a barren spell of six years without any piece of silverware.

Arsene Wenger was slightly handicapped with funds being at a minimum whilst rivals such as Manchester United, Chelsea and a newly backed Manchester City were on the scene, spending a premium on transfers in recent years. However, the Gunners found themselves with an excellent chance to secure silverware when they reached the League Cup final to face Birmingham City in 2011.

Birmingham City were set for a season of struggle in 2010/11, and eventually the Blues found themselves back in the Championship and have not returned to the top flight. So all signs pointed towards an Arsenal win...

The game at Wembley highlighted the pressure that Arsenal were under at the time, and the Gunners, for lack of a better word, crumbled on the big stage. Birmingham City took a shock lead through Nikola Zigic in the 29th minute but the lead was cut ten minutes later by Robin van Persie.

In the dying seconds, a defensive disaster from Laurent Koscielny and Wojciech Szczesny allowed former Inter Milan striker Obafemi Martins to score the winner.

Birmingham City were victorious and Arsenal's wait for a trophy would extend for another three years.

After their 2-1 final defeat in the previous season, Arsenal had a huge chance to redeem themselves after being drawn against League 2 side Bradford City in the fifth round of the 12/13 League Cup. A Garry Thompson goal gave the home side a surprise lead and with a late goal from Thomas Vermaelen keeping Arsenal in the tie. The game went to penalties with Arsenal skipper and goalscorer Thomas Vermaelen missing his penalty to seal a famous result for Bradford and an embarrassing exit for Arsenal.

The 1969 League Cup final between Swindon Town and Arsenal is historic as it is the last time that a domestic competition was won by a team outside of England’s top 2 divisions. The Arsenal side suffered from a flu virus ahead of the final at Wembley to give Swindon the advantage before kick off. With the first half finishing 1-1 the game went to extra time with Don Rogers scoring 2 goals to seal a 3-1 victory for Swindon.

For their League Cup game against third tier York City Manchester United’s team was full of young stars such as: David Beckham, Ryan Giggs and Phil Neville as well as well as established players like: Lee Sharpe and Gary Pallister, but that wasn’t enough to get through to the next round as they suffered an embarrassing 3-0 home defeat. With Alan Hansen famously saying “you’ll never win anything with kids” it looked at the time he was correct, although his damning words will continue to haunt him after how the young player at United stepped up in the seasons to follow.

Southend United pulled off a massive shock when then knocked out holders Manchester United back in 2006. The United side possessed enough quality to win the game with both Wayne Rooney and Cristiano Ronaldo playing in the game, but a stunning free kick from Freddy Eastwood gave Southend a huge win and progressed to the quarter-finals of the League Cup.