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Top Five: League Cup shocks

22 Sep 2010 12:32:36

Top Five: League Cup shocks

Following Everton's surprise penalty shoot-out defeat to Brentford in the Carling Cup last night, Football.co.uk's Joe Strange casts his mind back over five of the biggest upsets in the competition's history.

- Carling Cup Results / Tonight's Carling Cup Fixtures

Southend 1-0 Manchester United, November 7th 2006


A magnificent performance from Championship strugglers Southend gave them a famous 1-0 victory over Premier League giants and holders of the League Cup, Manchester United.

Freddy Eastwood's stunning free-kick put the Shrimpers ahead, but they had to rely of the brilliance of goalkeeper Darryl Flahavan to stop Cristiano Ronaldo from levelling the tie. Wayne Rooney was booked as a strong United side, also containing the likes of Gabriel Heinze, Darren Fletcher and Alan Smith, fell at the last-16 stage.

Burnley 2-0 Arsenal, December 2nd 2008

Despite Arsene Wenger fielding his usual team of youngsters, Burnley's comfortable 2-0 victory shocked many after Arsenal's impressive run to the quarter-finals.

A brace from Scottish midfielder Kevin MacDonald saw the Clarets safely through to a last four showdown with the Gunners' north London rivals Tottenham - a test that would ultimately prove too much for Owen Coyle's unfashionable side. Despite their semi-final loss, the Championship side still took a number of scalps during their cup run, most notably those of Premier League sides Fulham and Chelsea.

Swindon Town 3-1 Arsenal, March 15th 1969

Arguably the greatest acheivement in the club's history, Swindon's League Cup final victory over Arsenal is still sung about at the County Ground today.

The third division side did superbly to take first division giants Arsenal to extra-time, before winger Don Rogers popped up with a priceless double to take the trophy back to Wiltshire. Just two years later Arsenal completed a league and cup double.

Liverpool 1-2 Grimsby Town, October 9th 2001

After a goal-less 90 minutes, first division strugglers Grimsby Town looked down and out as a Gary McAllister penalty put Liverpool 1-0 up at the start of extra-time. But the Football League side refused to give up, as Marlon Broomes' equaliser silenced the Kop with a penalty shoot-out fast approaching.

Boyhood Liverpool fan and former Everton player Phil Jevons had other ideas, scoring a stunning last minute winnner from 30 yards to clinch Grimsby's first victory at Anfield in 24 visits.

Manchester United 0-3 York City, September 20th 1995

A United side containing David Beckham, Ryan Giggs and Phil Neville were on the end of one of the greatest giant-killings in League Cup history as York City picked up a comprehensive 3-0 win at Old Trafford.

Two goals from City striker Paul Barnes gave his side a commanding lead, before Tony Barras completed the rout. Sir Alex Ferguson's side won the return leg 3-1 at Bootham Crescent but that wasn't enough to see them through after their first-leg demolition.


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