Liverpool’s Cupset at Plymouth – Was It Their Worst Ever?

by
Virgil Van Dijk
Cosmin Iftode | Bigstockphoto

The quadruple was always going to be a tough ask for Liverpool, but few predicted their ambitious hopes would be shattered by Plymouth Argyle. Despite being rock bottom of the Championship at the time and odds-on favourites to face the drop, the Pilgrims ended up with a gigantic scalp.

To give you a sense of just how surprising this defeat was, coming into the match, the Reds had only lost 3 of 37 games under Arne Slot. You could back the visiting side at odds of 1/12 to progress to the fourth round, giving them an implied chance of winning of 92.3%. Despite looking like a complete mismatch, featuring two teams separated by 43 places in the footballing pyramid, Plymouth deservedly secured a 1-0 win.

This is not the first time Liverpool have been on the receiving end of a shock cup exit, though. As the list below will show, the Reds have been humbled on several occasions by lower-league opposition in the FA Cup, often at Anfield. At least some of the games on this list represent a bigger upset than the recent defeat to Plymouth.

Worcester City 2 – 1 Liverpool (1959)

A long time ago, but this still stands as one of Liverpool’s most embarrassing FA Cup defeats. Southern League Worcester had already caused a stir by punching above their weight to beat Fourth Division Millwall 5-2, and their reward was a tie against the Reds. Despite their earlier heroics, nobody was expecting the minnows to go toe-to-toe with a Second Division outfit. They did exactly this though, opening the scoring early on and refusing to crumble when Liverpool levelled. The winning goal came in the 81st minute as Dick White’s attempted clearance somehow managed to lob his own goalkeeper, sending most of the 15,111 crowd into a state of pure jubilation.

Liverpool 0 – 2 Bolton (1993)

Liverpool had avoided something of a shock by fighting back from two goals down the first time they met Bolton in the 1992/93 FA Cup third round. Ian Rush’s late strike gave the reigning FA Cup champions a lifeline in the form of a replay to be played at Anfield. Despite having home advantage on the second attempt, there would be no comeback this time. John McGinlay and Andy Walker scored the goals for the visitors, although it was David Lee who received much of the credit for his truly exceptional performance.

Liverpool 0 – 1 Bristol City (1994)

Another year and another FA Cup defeat to second-tier opposition in front of their own fans. This time it was Bristol City who dealt the decisive blow and it was a game which marked the end of Graeme Souness‘s time as Liverpool manager. Souness had been under fire, but avoiding a cup upset might have seen him keep his job a little longer. A 1-1 draw at Ashton Gate saw the tie head to a replay and on Merseyside Brian Tinnion’s effort was enough to separate the two sides. Liverpool, to their credit, were not sore losers as Neil Ruddock gifted the City players a crate of beer in the dressing room.

Liverpool 0 – 1 Blackburn Rovers (2000)

Liverpool’s final realistic shot of silverware in the 1999/00 season came to a surprise end as they slipped to a home defeat to recently relegated Blackburn Rovers. It had been an awful 12 months for Rovers, but they were able to savour their trip to Anfield, the ground where they had clinched the Premiership title back in 1995. A combination of wasteful finishing and excellent goalkeeping had kept the game goalless but with five minutes to spare it was the under-pressure visitors who, through Nathan Blake, managed to convert a rare foray into the Liverpool box.

Liverpool 0 – 1 Crystal Palace (2003)

Julian Gray’s stunning effort put the visitors ahead in this clash but just 15 minutes later, Palace were down to 10 men as Dougie Freedman caught Sami Hyypia with an elbow. With the numerical advantage, higher division status and home crowd roaring them on, surely the next goal in the game would be Liverpool’s? While many thought so, Palace unexpectedly extended their lead via a Stephane Henchoz own goal. The visitors even managed to retain their clean sheet thanks to an exceptional performance from Cédric Berthelin, who was only brought in as Alex Kolinko refused to play the previous weekend.

Burnley 1 – 0 Liverpool (2005)

Defeat away at a middling Championship team is far from the biggest FA Cup upset Liverpool have experienced, but the comical nature of loss means it deserves inclusion on this list. Djimi Traore, who months later helped Liverpool to victory in the Champions League final, scored one of the most curious own goals you are likely to see. A low ball fired into the box arrived at the feet of the Malian, who under no real pressure, spun on the ball and slotted it past Jerzy Dudek.

Liverpool 1 – 2 Barnsley (2008)

A bright start, which eventually resulted in a Dirk Kuyt goal after 32 minutes, suggested this would be a routine win for the home side. The only reason the scoreline remained close was the heroics of debutant Luke Steele, signed on an emergency loan deal just two days earlier. Against the run of play, Barnsley found an equaliser and Liverpool responded with an even bigger assault on their goal. Steele and the Barnsley defence continued to stand firm though and this allowed Brian Howard to fire home a famous winner from the edge of the box.

Oldham Athletic 3 – 2 Liverpool (2013)

Most teams on this list were playing in the second tier when defeating Liverpool but Oldham Athletic are one of the exceptions. Despite the two clubs being separated by two divisions, the Latics managed to fire home three goals against their more illustrious opponents. The Reds named a strong side including Luiz Suarez and Raheem Sterling but struggled to cope with Oldham’s direct approach. Their first and third goals for the hosts came via headers, while the second came as a result of Brad Jones spilling a cross.

Plymouth Argyle 2 – 1 Liverpool (2025)

The mistake Arne Slot made for this was resting too many players. The Dutchman made 10 changes to the starting XI which hammered Tottenham 4-0, as he thought he could get away with resting a few names. On another day, perhaps he would have done but lower division sides have shown they can be tough opponents to Premier League foes who name a second-string side. Although the visitors created little, Darwin Nunez had a glorious moment to equaliser but Conor Hazard‘s big save ensured there would be no penalty shootout drama.