Ranked: Liverpool's worst defeats of the Jurgen Klopp era

Date: October 4, 2020

Competition: Premier League

Liverpool conceded seven goals for the first time since 1963 when they were taken apart by a rampant Aston Villa at the start of the 2020-21 campaign.

The Reds were without Alisson due to injury and brought in Adrian in goal. The stand-in stopper was, however, picking the ball out of his net after just four minutes as Ollie Watkins scored his first ever Premier League goal.

Watkins ended up going home with the match ball after completing his hat-trick before the half-time whistle had even been blown.

John McGinn and Ross Barkley were also on target along with Jack Grealish. The Villa captain ended the game with a hat-trick of assists and two goals as Villa secured an incredible win against the defending Premier League champions.

Date: February 21, 2023

Competition: Champions League

Liverpool's loss to Real Madrid will live long in the memory for Reds' fans for all the wrong reasons.

The night started out perfectly for Klopp's side. A brilliant flicked goal by Darwin Nunez was followed by Mohamed Salah taking advantage of a howler from Thibaut Courtois that left the Reds 2-0 up and in dreamland after just 14 minutes.

Yet Madrid roared back to life and then some. Vinicius Junior halved the deficit in some style with a fine shot before Alisson followed in Courtois' footsteps and gifted the hosts an equaliser.

Liverpool proceeded to simply fall apart in the second half as the defending European champions put on a show to ease to an emphatic victory and all but book themselves a place in the quarter-finals.

Eder Militao headed the visitors into the lead before Ballon d'Or winner Karin Benzema grabbed a brace to put the icing on Real Madrid's cake.

Date: September 9, 2017

Competition: Premier League

Liverpool headed to the Etihad Stadium at the start of the 2017-18 campaign fresh from an impressive 4-0 win at home to Arsenal.

However, the Reds were promptly taken apart by Pep Guardiola's side, who put in an ominous showing.

Sergio Aguero gave the hosts an early lead to put City on top in the game. The Reds then suffered another blow before half-time when Sadio Mane saw red for a high challenge on Ederson.

City took full advantage of the extra man to coast to victory, as Gabriel Jesus and Leroy Sane both scored twice to hand the Reds and Klopp a heavy defeat.

Date: January 14, 2023

Competition: Premier League

Klopp ranked Liverpool's defeat at the Amex Stadium as the worst game of his managerial career after seeing his team comfortably beaten on the south coast.

The Seagulls handed World Cup winner Alexis Mac Allister his first start since returning from Qatar and turned in a superb performance that heralded a fully deserved three points.

Solly March scored twice and former Manchester United striker Danny Welbeck was also on target as Brighton moved above Liverpool in the table with the win.

Date: December 20, 2015

Competition: Premier League

One of the worst defeats in Klopp's early months at Liverpool came at Vicarage Road against newly-promoted Watford.

Goalkeeper Adam Bogdan had a debut to forget, dropping an early cross with his first touch to gift the Hornets an early opener through Nathan Ake.

Odion Ighalo doubled Watford's lead with a shot that flew in off the post and then headed the hosts' third to make it a miserable afternoon for Klopp.

Date: January 20, 2021

Competition: Premier League

Carlo Ancelotti seems to enjoy taking on Klopp and came up trumps again when the two met in a Merseyside derby back in 2021.

Liverpool have dominated their near neighbours in recent years, but suffered a shock reverse at Anfield, as Ancelotti masterminded a first away Everton win in the derby since 1999.

The Toffees took the lead when James Rodriguez teed up Richarlison to beat Alisson. Gylfi Sigurdsson then finished off Liverpool from the penalty spot after a foul by Trent Alexander-Arnold.

It was a memorable win for the Toffees, and a result that also made it four defeats in row for Liverpool as their title defence fell apart.

Date: February 7, 2021

Competition: Premier League

Pep Guardiola picked up his first win at Anfield as a manager in 2021 in what was also City's first victory away at Liverpool since 2003

The visitors saw Ilkay Gundogan miss an early penalty but still managed to score four times, with a little help from goalkeeper Alisson.

The Brazilian had a day to forget with two mistakes that produced goals for Gundogan and Raheem Sterling, while Phil Foden compounded Alisson's misery by smashing home City's fourth.

Date: January 2, 2023

Competition: Premier League

Brentford beat Liverpool for the first time since 1938 as the Reds put in another dismal defensive showing during the 2022-23 campaign.

The Bees were without top scorer Ivan Toney due to injury but still put past three past Klopp's side at the Community Stadium and created many more chances.

An own goal from Ibrahima Konate sent the visitors on their way to defeat, although VAR saved the Reds from conceding two more via set-pieces.

Yet Brentford were not to be denied, and goals from Yoane Wissa and Bryan Mbeumo secured a famous win for Thomas Frank's side.

Date: September 7, 2022

Competition: Premier League

Liverpool's Champions League campaign got off to a disastrous start with a 4-1 hammering in Italy against Napoli.

Piotr Zielinski, Andre-Frank Zambo Angiussa, and Giovanni Simeone had the hosts 3-0 up at the break, but they could have led by an even bigger scoreline. Goalkeeper Alisson saved a penalty from Victor Osimhen and Virgil van Dijk made a crucial goalline clearance from Khvicha Kvaratskhelia.

The Reds will have been relieved to see Osimhen depart just before half-time due to injury, but conceded again after the break when Zielinski scored his second of the night.

Date: February 29, 2020

Competition: Premier League

Klopp endured another miserable defeat to Watford in 2020 as the Hornets ended his team's 18-match unbeaten Premier League run.

Another victory would have made it the longest winning streak in English top-flight history, but Liverpool were played off the park instead.

Watford started the game in the relegation zone but put on a show. Ismaila Sarr poked home the opener and then lifted the ball over Alisson to make it 2-0. Troy Deeney then curled home a fine third to seal a famous win in style.

Date: October 22, 2017

Competition: Premier League

Over 80,000 fans packed in to Wembley Stadium to see Tottenham crush Liverpool 4-1 back in 2017.

Mauricio Pochettino's men had failed to win any of their first three league fixtures in their temporary home, but saw off the Reds in a commanding display.

Two goals from Harry Kane, another from Son Heung-min and a Dele Alli strike did the damage as Spurs capitalised on an error-strewn performance from the Reds.

Date: May 1, 2019

Competition: Champions League

Liverpool would go on to win their Champions League semi-final tie against Barcelona in 2019, but had to do it the hard way after being beaten 3-0 in the first leg at the Camp Nou.

Lionel Messi scored twice, including a brilliant free-kick, and Luis Suarez was also on target against his former side in a dramatic tie.

Ernesto Valverde's should have finished the game with a bigger advantage, too, as Ousmane Dembele wasted a glorious late chance to make it 4-0 which could well have killed the tie off.

He didn't and the Reds produced a miracle comeback at Anfield to progress.