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10 Greatest League Cup ‘upsets’ - featuring Arsenal, Manchester United, and more

After Leeds United’s 2-1 victory over Everton on Tuesday, is this year’s League Cup set for another round of upsets? Here are my all time top ten League Cup shock, and Liverpool also feature as well as United and Arsenal.

At 10, is Sheffield Wednesday’s victory over Manchester United in the 1991 League Cup Final. A powerful volley from Wednesday’s John Sheridan was enough to win his side the trophy against the FA Cup holders under Sir Alex Ferguson’s early reign.

Our number 9 spot is occupied by last year’s game between Premier League newbies Norwich City at home to the MK Dons who won 0-4 after some shocking defending from the side then managed by Paul Lambert who suffered his worst defeat of his two-year spell at Carrow Road.

Down to 8 and it’s another upset for Sir Alex’s Manchester United – this time away from home to the Championship’s Southend United, who scored the only goal of the game – a driving free-kick from Freddy Eastwood saw the likes of Cristiano Ronaldo and Wayne Rooney humbled as the League Cup holders were defeated, crashing out of the cup in 2006.

Creeping in at 7 is the 1967 Final, the first ever to be played at Wembley. QPR, then third division underdogs beat fist division West Brom 3-2 in a thrilling contest that made history for QPR who became the first third-tier side to win a major English trophy.

At 6, it’s Liverpool’s 2001 defeat at Anfield to Grimsby Town. Again, the holders crashed out of the competition thanks to two extra-time wonder strikes from Marlon Broomes and Phil Jevons, the latter a lifelong Liverpool fan – he’ll surely never live it down.

Into our top 5, and it’s our first penalty shoot out win – for Burnley who snatch a Fourth Round victory from Chelsea in front of the Stamford Bridge faithful. The game went to extra time after Ade Akinbiyi equalized for the visitors who had trailed all game to a Didier Drogba goal.

The Blues had a goal disallowed, after squandering a string of chances to put the game to bed. The game went to penalties and after Burnley had scored all of their five penalties, and Chelsea all four of theirs, Jon Obi Mikel stepped up to take his – on target but saved by Clarets goalkeeper Brian Jensen – a game he’s unlikely to forget.

At 4, Arsenal 1 and Walsall 2 in the 1983 clash that paved the way for George Graham to take the reigns from Terry Neill who was well on his way to being sacked before what should have been an easy game for his Gunners – instead Walsall only exacerbated his troubles at Highbury and it was to be one of his final games in charge.

Edging in to our 3rd spot is another penalty shoot-out surprise – this time it was Liverpool who were humbled, at home to League Two side Northampton Town in 2010. The Kop surely thought the game was a foregone conclusion but it ended in despair for the Reds, tied 1-1 after 90 minutes, and 2-2 after a late equalizer from David N’Gog in extra-time.

But N’Gog wasn’t to be the hero just yet, as he missed his penalty, along with Stephen Guinan and Nathan Eccleston, whose fifth spot-kick hit the crossbar. Abdul Osman stepped up and his textbook drive left the Anfield faithful with their head in their hands, not for the first or last time under Roy Hodgson.

Our ‘nearly-men’ at number 2 are York City who embarrassed Manchester United in a 0-3 thrashing at Old Trafford in 1995. The United boss took some stick for fielding a team of youngsters - David Beckham, Paul Scholes and Phil Neville were brought in alongside first-teamers Ryan Giggs and Gary Pallister but failed to make the grade with a match all of the above could possibly be forgiven for – maybe they owe their careers to York, who certainly taught them a thing or two about defending.

And, finally, our most ‘upsetting’ of ‘upsets’ is the 1969 League Cup final between Swindon Town and Arsenal. The Gunners might have guessed it wasn’t going to be their day as the Robins took an early lead thanks Roger Smart’s outsmarting of the clumsy Arsenal backline.

The underdogs managed to defend their 1-0 lead until the 86th minute when their hopes of victory were seemingly dashed by Bobby Gould, who took advantage of yet another goalkeeping error to equalize.

Swindon miraculously took the lead again in extra-time, as Dan Rogers punished sloppy defending from a corner. He went on to score his side’s third as their counter-attack worked tactics worked to perfection – Rogers coolly rounding the Arsenal goalkeeper to settle the match at 3-1.

image: © Magnus D

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