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Liverpool's Five Biggest Ever League Cup Upsets

Karl MatchettAug 8, 2013

The draw for the second round of the Capital One Cup was made on Thursday, with Liverpool one of the teams taking part thanks to their failure to qualify for European football this season.

Notts County are the side that Brendan Rodgers' team will face at Anfield in the last week of August. It will no doubt be billed as the usual "David vs. Goliath" type of tie, with the away side currently playing in League One, the third tier of English football.

Having been disappointing in the domestic cups last season, Rodgers and his side will want to do better this time around, meaning they'll have to be both professional and committed when they come up against Notts County to avoid a giant-killing.

That, of course, would not  be the first time an upset has happened to the Reds in this competition in all its many guises. Here are five of the biggest shocks for Liverpool in the League Cup.

Tottenham Hotspur, 1984

1 of 5

In season 1984-85, Liverpool and Spurs finished second and third respectively in the First Division league table, both ending on 77 points.

With the two teams so close, it's fair to ask, what makes this defeat such an upset?

Well, it wasn't the fact that Spurs were a smaller club this time, but instead that this was the first League Cup match that Liverpool had lost in an amazing four years and nine months. The Reds were dominant in the competition in the early 1980s, winning it a record four times in a row from 1981-84, even beating Spurs themselves in the 1982 final at Wembley.

In October 1984, however, the Reds went out at the third round stage thanks to a 1-0 defeat at White Hart Lane as they finally relinquished their grip on the trophy. Clive Allen scored the early goal to consign the Reds to defeat, with the team featuring the likes of Alan Hansen, Ian Rush, Phil Neal and Bruce Grobbelaar.

Liverpool lineup: Grobbelaar, Neal, A. Kennedy, Lawrenson, Whelan, Hansen, Robinson, Lee, Rush, Johnston, Gillespie. Sub: Wark.

Peterborough United, 1991

2 of 5

The Reds didn't win the League Cup again after that defeat at Spurs for the rest of the decade, but a favourable draw to play Peterborough United in the fourth round of the 1991-92 campaign gave Liverpool a chance of a good cup run once more.

The London Road side were languishing in the bowels of English football at the time in the old Fourth Division, so the Reds were expected to brush them aside with ease.

Of course, it didn't happen that way, as Graeme Souness' team suffered a humiliating 1-0 defeat.

Garry Kimble scored the only goal of the game early in the first half, with the Reds unable even to put a single goal past the side playing three divisions below them.

Liverpool lineup: Grobbelaar, Ablett, Burrows, Nicol, Wright, Tanner, Saunders, Houghton, McManaman, Molby, Marsh. Subs: Harkness, Redknapp.

Middlesbrough, 1998

3 of 5

Well into the Premier League years now and Liverpool faced—and were knocked out by—Middlesbrough two years in a row.

First, in 1997, Boro won 2-1 at the Riverside Stadium in the year they were relegated from the top flight; bad enough, sure, but the very next campaign Liverpool faced Boro again, this time as a Division One team in a two-legged semi-final. Boro were a side on the cusp of promotion and they beat Liverpool soundly over 180 minutes.

Liverpool won the first leg 2-1 with Jamie Redknapp and Robbie Fowler scoring for the Reds of Anfield and Paul Merson getting Boro's consolation. In the return leg, Roy Evans' team fell behind to two goals in the opening five minutes. Merson got Boro off to the perfect start with a goal in only two minutes and Marco Branca doubled their lead two minutes later.

The Reds failed to find a reply to take the game to extra time and were knocked out at the last four stage, while Middlesbrough went on to the League Cup final and eventual promotion back to the Premier League.

Liverpool lineup: James, Jones, Harkness, Bjornebye, Matteo, McManaman, Ince, Carragher, Fowler, Berger, Owen. Subs: Friedel, Leonhardsen, Riedle.

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Grimsby Town, 2001

4 of 5

The turn of the millennium brought better fortunes for Liverpool as they won the League Cup in 2001 under Gerard Houllier, their first triumph in the tournament since 1995.

However, in the 2001-02 season as defending champions, the Reds put up a limp defence of their crown and they bowed out at the first attempt following a dismal 2-1 defeat—at Anfield of all places—against lowly Grimsby Town.

Fighting relegation from Division One at the time, Grimsby came to Liverpool's home turf and not only kept the Reds at bay for 90 minutes, forcing extra time, but even came from behind during the additional 30 minutes to turn the tie around and knock out the holders.

Gary McAllister's penalty in the first half of extra-time should have been more than enough, but Marlon Broomes and Phil Jevons—a former Everton youth player and Liverpool supporter—struck before the final whistle to stun the Reds, and out they went.

Liverpool lineup: Kirkland, Hyypia, Carragher, Vignal, Wright, Smicer, Murphy, Hamann, Barmby, McAllister, Litmanen. Subs: Dudek, Kippe, Redknapp, Berger, Heskey.

Northampton Town, 2010

5 of 5

Not much went right for Roy Hodgson during his brief reign as manager of Liverpool in the 2010-11 season, but one of his lowest moments certainly came at Anfield in the League Cup.

Liverpool took on Northampton Town, who went on to end the season in 16th place in League Two, at home in the third round of the competition that season. On a miserable, wet and disappointing night in the famous old stadium, which was barely half-full, Northampton out-fought and out-played the Reds before beating them in a penalty shoot-out.

Milan Jovanovic got Liverpool off to a good start with an early goal before Billy McKay equalised just after half-time. With 90 minutes up and the scores level, the two teams went into extra time where they both found another goal—Michael Jacobs gave Northampton the lead before David Ngog levelled for the Reds with just four minutes left.

Ngog and Nathan Eccleston missed their spot kicks, Daniel Agger and Jonjo Shelvey scored, but Northampton scored four out of their five to take the tie 4-2 on penalties.

Thankfully, Liverpool bounced back to win the competition outright the following season under Kenny Dalglish, and this dreadful defeat to the Cobblers remains the Reds' last cup upset in the competition they have won more times than any other club.

Liverpool lineup: Jones, Agger, Kyrgiakos, Wilson, Kelly, Pacheco, Babel, Lucas, Spearing, Jovanovic, Ngog. Subs: Hansen, Wisdom, Robinson, Shelvey, Eccleston, Ince, Amoo.

Match data and lineups courtesy of LFChistory.net.

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