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10 biggest upsets in the League cup

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MK Dons 4-0 Manchester United - 2014

Starting off our list we’ve got 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.

Oxford United 4-0 West Ham - 2019

The most recent game on this list is West Ham’s embarrassing exit after losing 4-0 away at League 1 side Oxford United yesterday evening. After comfortably beating Manchester United only 3 days earlier you would have thought their game against Oxford would have been light work, however, goals from Elliott Moore, Matt Taylor, Tarique Fosu and Shandon Baptiste meant otherwise and West Ham’s 39 years wait for a trophy is looking like it will continue.

Liverpool 2-2 Northampton (2-4 on pens) - 2010

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.

Colchester 0-0 Tottenham (4-3 on pens) - 2019

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 1-2 Birmingham City - 2011

Arsenal’s League Cup final against Birmingham City in 2011 was their chance to end their 6 year wait for a trophy, but Birmingham City had other ideas with a late goal from Obafemi Martins sealing a 2-1 win for Birmingham City and gave them their second League Cup.

Bradford 1-1 Arsenal (3-2 on pens) - 2012

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.

Swindon Town 3-1 Arsenal - 1969

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.

Manchester United 0-3 York City - 1995

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.

Notts County 3-0 Tottenham - 1994

Despite the likes of Teddy Sheringham and Jurgen Klinsman being a part of the squad back in 1994 Tottenham weren’t short of goals, however that wasn’t enough after their embarrassing 3-0 defeat away to a Notts County side that would be relegated at the end of the season and would go through three managers in the process.

Southend United 1-0 Manchester United - 2006

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.