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The Biggest Shock Results in Liverpool’s History

One thing is for sure – there’s never a dull moment as a Liverpool fan. With their penalty triumph over Chelsea in August’s Super Cup, Liverpool confirmed themselves as the most decorated club in England, their 43 trophies just pipping Manchester United’s 42. But it hasn’t always been plain sailing for the Reds.
Anfield has seen its fair share of ups and downs – and when we say ups and downs, we sure mean it. More peaks and troughs than an Alton Towers rollercoaster, more highs and lows than a Pavarotti opera, more adrenaline than a session at Winningroom Slots. Liverpool’s chequered history in cups both domestic and European is a site to behold – so here are five of their biggest shocks of all time.
5) Grimsby Town, 2001
Earlier on in 2001, Gerard Houllier had led his Liverpool team to glory over Birmingham at Wembley, lifting the League Cup alongside the FA Cup and the UEFA Cup to complete an impressive treble. However, their defence of the former fell to pieces at the first hurdle the following season, as lowly Grimsby – fighting off relegation to Division Two at the time – stunned them at Anfield.
After a dour stalemate for 90 minutes, Gary McAllister’s penalty put the Reds ahead in extra time, before Marlon Broomes equalised with just seven minutes to go. Virtually the last kick of the game was a wonder strike by boyhood Liverpool fan Phil Jevons, who consigned his erstwhile favourites to an ignominious defeat.
4) Oldham Athletic, 2013
An equally remarkable giant killing came 12 years later, when a Liverpool team containing the likes of Luis Suarez, Daniel Sturridge and Raheem Sterling travelled to Oldham Athletic in the FA Cup. Despite those glittering names up front so nearly earning Liverpool a Premier League title that same year, they could do nothing against their League One counterparts.
Matt Smith scored a memorable double for the hosts, his goals sandwiching Luis Suarez’s solo effort, and Reece Wabara made things slightly more comfortable with a back-post header. Liverpool rallied, bringing on Steven Gerrard with just over half an hour on the clock, and though their talisman helped to conjure a goal for Joe Allen to make the final minutes tense ones, Oldham held on for a memorable win.
3) Barcelona, 2019
Shocks aren’t always bad news for the reds. After a spirited run to the final of the Champions League in 2018, Liverpool were looking to go one better last time out. After dispatching Bayern Munich and Porto in the previous knockout rounds with the minimum of fuss, they seemed to be on course to do just that – but a 3-0 trouncing away at the Camp Nou to Barcelona in the semi-finals looked to have put the brakes on their charge for the title.
However, an incredible performance at Anfield, marked by braces for unsung heroes Divock Origi and Georginio Wijnaldum, saw Liverpool prevail 4-3 on aggregate and advance to the final in Madrid. In a largely lacklustre game, they swept aside compatriots Tottenham Hotspur to claim their sixth European Cup trophy.
2) Worcester City, 1959
Rewind 60 years and things didn’t always go Liverpool’s way. Although the Reds weren’t currently playing in the top flight at the time of this game against Worcester City in the FA Cup, they were pushing hard for promotion and were expected to easily swat aside their non-league opposition. Worcester were playing in the third round for the very first time and eight of their starting eleven had been working at their day jobs before taking to the field that evening.
Even so, their pluck and determination were enough to see off Phil Taylor’s Liverpool 2-1. Teenage winger Tommy Skuse opened the scoring with 10 minutes on the clock, while Dick White put the ball into his own net near the end of the game to double Worcester’s advantage. A late Geoff Twentyman penalty could not save the game for the Reds, who suffered one of their biggest ever upsets.
1) AC Milan, 2005
No list of Liverpool’s shock results would be complete without a mention of their heroics in Istanbul in 2005. The game got off to the worst start imaginable when 36-year-old Paolo Maldini became the oldest player to score in a Champions League final within the first minute of the game. Shortly before half-time, Hernan Crespo double made it 3-0 to Milan going into the break. Facing this seemingly insurmountable task, Liverpool rose to the challenge admirably.
Within five incredible second half minutes, Gerrard, Vladimir Smicer and Xabi Alonso all scored to make honours even, setting the game up for an unbearably tense final half hour. Neither side could break the deadlock further, so the game was decided on penalties. Polish goalkeeper Jerzy Dudek became the hero in the shootout, denying Andrea Pirlo and Andriy Shevchenko to hand Liverpool a famous 3-2 victory on penalties.

Written by Alan Spencer

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