Tottenham suffered a shock Carabao Cup shootout defeat to League Two side Colchester United on Tuesday night. Despite naming a strong side, Mauricio Pochettino’s men failed to breakdown the U’s, with the tie going straight to penalties after a goalless 90 minutes. Christian Eriksen and Lucas Moura both missed from the spot, which allowed Colchester defender Tom Lapslie to seal a memorable win for John McGreal’s side. Following Spurs’ dramatic exit, we’ve taken a look at some of the biggest cup upsets of all time.
Manchester United 0-1 Leeds (2010)
Jermaine Beckford’s goal gave League One side Leeds United a famous FA Cup win over Manchester United at Old Trafford. The loss was the first time United had been knocked out in the third round under the management of Sir Alex Ferguson, and the first time that the Scot had seen his side eliminated by a lower division side.
Liverpool 2-2 Northampton (2-4 pens) (2010)
League Two’s Northampton Town dumped Liverpool out of the Carling Cup back in 2010 thanks to Abdul Osman’s decisive spot-kick. Roy Hodgson decided to give various Reds youngsters a chance at Anfield, however, after an initial 2-2 draw, Hodgson was left to rue his selection decisions.
Burnley 0-1 Lincoln City (2017)
National League side Lincoln City became the first non-league side to reach the quarter-finals of the FA Cup since 1914 by defeating Burnley at Turf Moor. Sean Raggett was the Imps’ hero as his late header stunned the top-flight side in front of their own supporters.
Manchester United 0-3 York City (1995)
Second division side York City stunned Manchester United at Old Trafford in the first leg of their second-round League Cup tie in 1995. Two goals from Paul Barnes and one from Tony Barras was enough to defeat Sir Alex Ferguson’s young side, with the Minstermen progressing 4-3 on aggregate despite a 3-1 second-leg defeat.
Liverpool 1-2 Barnsley (2008)
Barnsley consigned Liverpool to a shock FA Cup exit at Anfield back in 2008. Dirk Kuyt gave the home side a lead but Stephen Foster headed home Martin Devaney’s cross to level the tie. Barnsley goalkeeper Luke Steele played out of his skin to keep the Reds at bay before Brian Howard netted a quite remarkable injury-time winner for the visitors, leaving the home fans in stunned silence.
Notts County 3-0 Tottenham (1994)
Despite fielding the likes of Jurgen Klinsmann, Sol Campbell and Teddy Sheringham, Tottenham fell to an embarrassing 3-0 defeat against First Division side Notts County back in 1994. The result piled the pressure on boss Ossie Ardiles, who was sacked shortly after.
Oldham 3-2 Liverpool (2013)
A 3-2 loss at Oldham in 2013 with a team featuring the likes of Raheem Sterling, Steven Gerrard and Luis Suarez for Liverpool has to be up there. Possibly one of Oldham’s greatest FA Cup moments, as they completed a giant-killing whilst scrapping to avoid relegation to League Two. They came out in excellent form and deserved their place in the next round.
Southend 1-0 Manchester United (2006)
Championship strugglers Southend United dumped holders Manchester United out of the League Cup and progressed into the last eight back in 2006. Sir Alex Ferguson started both Wayne Rooney and Cristiano Ronaldo, however, it was Freddy Eastwood who proved to be the difference.
Chelsea 2-4 Bradford (2015)
Gary Cahill and Ramires had the Premier League leaders 2-0 up in 2015 but League One outfit Bradford stunned their hosts with goals from Jon Stead, Filipe Morais, Andy Halliday and Mark Yeates to earn a place in the last 16.
Peterborough United 1-0 Liverpool (1991)
Liverpool won the FA Cup in 1992, however, earlier that season, Graeme Souness’ side suffered a shock fourth-round League Cup defeat to Peterborough United. The Third Division underdogs stunned the Reds thanks to Gary Kimble’s first-half strike.
Leicester City 1-2 Wycombe Wanderers (2001)
One of the most remarkable FA Cup stories ever is that of Roy Essandoh. Wycombe were so short of attackers that they posted an advert on Ceefax asking for any strikers to come on trial. Essandoh answered the call and was given a rolling contract. In an astonishing turn of events, the striker came off the bench and scored a 90th-minute goal to put his side in the semi-finals.
MK Dons 4-0 Manchester United (2014)
Doubles from Will Grigg and Benik Afobe helped League One side MK Dons thrash Manchester United in the second round of the League Cup back in 2014. It was the first time the Red Devils had turned out in the second round for 19 years, and the result continued to heap pressure on Louis van Gaal.
Sutton United 2-1 Coventry (1989)
Just 18 months on from winning the FA Cup, Coventry City were knocked out by non-league Sutton United. Goals from Tony Rains and Matthew Hanlan knocked Coventry out. That remained the only occasion where a non-league side defeated a top-flight side for 24 years, until…
Norwich City 0–1 Luton Town (2013)
Substitute Scott Rendell scored six minutes after coming off the bench to give Conference side Luton a 1-0 win over Norwich. The Canaries became the first Premier League side to be knocked out of the FA Cup by a non-league side.
Bradford City 1-1 Arsenal (3-2 pens) (2012)
League Two side Bradford City pulled off one of the biggest League Cup shocks back in 2012, defeating Arsenal on penalties to reach the last four. Gunners skipper Thomas Vermaelen missed the crucial spot-kick which allowed The Bantams to advance, and they went on to reach the final after defeating Aston Villa in the semi-final.
Wrexham 2 -1 Arsenal (1992)
Arsenal were the reigning First Division champions in 1992 and were expected to easily dispatch Third Division Wrexham and things were going as planned when Alan Smith put the visitors 1-0 up. However, a great Mickey Thomas free-kick drew the Welsh side level, before Steve Watkin’s famous goal put Arsenal out.
Shrewsbury Town 2-1 Everton (2003)
Shrewsbury manager Kevin Ratcliffe was overjoyed as his side knocked out the club where he’d been so successful as a player. Nigel Jemson put the home side in front at Gay Meadow, but substitute Niclas Alexandersson looked to have saved Everton’s blushes. However, Jemson headed home with just two minutes left to give the Third Division side a famous victory.
Bournemouth 2-0 Manchester United (1984)
Third Division Bournemouth, managed by a young Harry Redknapp, pulled off a famous 2-0 third-round victory over Manchester United back in 1984. Goals from Milton Graham and Ian Thompson were enough to win the tie for the Cherries. After the game, Redknapp said: “It’s got to be the greatest day of my life, and I’m sure it’s the greatest day of all the players’ lives.”
Stevenage 3-1 Newcastle (2011)
League Two side Stevenage were enjoying their first season back in the Football League when they were drawn against Newcastle in the third round. Goals from Stacey Long, Michael Bostwick and Peter Winn gave the home side a much deserved win, knocking out Alan Pardew’s men.
Sunderland 1-0 Leeds (1973)
In one of the biggest FA Cup shocks in the history of the famous competition, Sunderland beat Leeds 1–0 in the final to become the first Second Division side to lift the Cup since West Brom back in 1931. Leeds had no reply to Ian Porterfield’s first half-goal, and as such, the trophy went to the North East side.
Wigan Athletic 1-0 Manchester City (2018)
Five years on from Wigan’s famous FA Cup win over Manchester City, the Latics pulled off a similar result at home. Wigan had been relegated twice since that final, whereas Man City had gone on to become of Europe’s most feared sides. The playing field was more level when Fabian Delph was sent off, and Wigan capitalised with their man advantage when Will Grigg slotted home in the 79th minute. City tried everything to grab an equaliser but were unable to find a way past Christian Walton.
Oxford United 3-2 Swansea City (2016)
League Two side Oxford United knocked Premier League Swansea out of the FA Cup, coming from 1-0 down in the process. Jefferson Montero put the Swans ahead, but Liam Sercombe’s penalty and a brace from Kemar Roofe sent the home fans into bedlam. Bafetimbi Gomis’ strike gave the Swans a lifeline but they couldn’t find an equaliser and as such, they were dumped out the cup.