Liverpool’s chances of reaching the quarterfinals of the Champions League are over after a shocking 5-2 home loss to Real Madrid.
The Reds watched a two-goal lead vanish in front of a boisterous home crowd as the defending champions went on the rampage.
Here, we examine the Merseysiders’ six worst losses at Anfield.
2010 Liverpool-Northampton draw (2-2 overall, 2-4 on penalties)
This was one of Liverpool’s darkest days, even taking into account how awful Roy Hodgson’s miserable brief tenure at the club was.
Visitors Northampton, who are currently 17th in League Two, outplayed the hosts, who fielded a depleted team, and prevailed in this Carling Cup third-round match.
David Ngog thought he had saved the Merseysiders’ blushes when he notched a 116th-minute equaliser, before the Frenchman and teenage substitute Nathan Eccleston missed their penalties in the shootout.
Liverpool were knocked out of the Carling Cup by Northampton in 2010
Liverpool were knocked out of the Carling Cup by Northampton in 2010
Liverpool 0-6 Sunderland, 1930
Division One strugglers Sunderland arrived at Anfield but never looked back from Bobby Gurney opening the scoring in the first minute.
The former miner went on to score four and was disappointed he did not make it five after putting a close-range finish over the crossbar.
George Lawley and Albert Wood scored the others in a result that remains Liverpool’s heaviest home defeat.
Liverpool 3-6 Arsenal, 2007
Julio Baptista scored four goals to silence Anfield in 2007
Julio Baptista scored four goals to silence Anfield in 2007
Seventy-seven years later, Arsenal striker Julio Baptista repeated Gurney’s feat with two goals in each half of this Carling Cup quarterfinal.
The hosts were 4-1 down at the break thanks to other goals from Jeremie Aliadiere and Alex Song and only late consolations from Steven Gerrard and Sami Hyypia prevented a heavier loss.
A stunned boss Rafael Benitez said after the game: “It is a bad night for us and all we can say is sorry to the supporters.
“Now is not the time to point the finger or look to blame people. We win together and we lose together.”
Liverpool 0-0 Grimsby (1-2 aet), 2001
Grimsby recorded an extra-time victory over Liverpool in 2001
Grimsby recorded an extra-time victory over Liverpool in 2001
League Cup holders Liverpool were knocked out by Championship strugglers Grimsby thanks to former Evertonian Phil Jevons’ 30-yard strike seconds from the end of extra-time.
Gary McAllister’s 101st-minute penalty broke the deadlock but Marlon Broomes’ equaliser set up the visitors’ first win at the ground in 24 visits.
The shock result brought to an end Liverpool’s unbeaten run in cup competitions since January 2000, having secured a League Cup, FA Cup and UEFA Cup treble in the 2000-01 season.
Liverpool 0-1 Bristol City, 1994
With their first meeting at Ashton Gate ending in a 1-1 draw after an abandonment and rearrangement due to floodlight failure, Liverpool welcomed Bristol City to Anfield for a FA Cup third-round replay in 1994.
Brian Tinnion’s 66th-minute strike for the second-tier opposition not only knocked out a Reds team featuring the likes of John Barnes, Ian Rush, Steve McManaman and Jamie Redknapp but also prompted the resignation of manager Graeme Souness days later.
The game epitomised a difficult season for the Anfield faithful, with their team finishing eighth in the Premier League, their lowest league position since the 1962-63 campaign.
Brian Tinnion was Bristol City’s hero at Anfield in 1994
Brian Tinnion was Bristol City’s hero at Anfield in 1994
Liverpool 2-5 Real Madrid (2023)
Fresh from 2-0 victories over Everton and Newcastle, Liverpool came into this Champions League last-16 tie buoyed by renewed optimism.
Early efforts from Darwin Nunez and Mohamed Salah sent Jurgen Klopp’s men into a 2-0 lead after 14 minutes to further raise spirits.
But braces from Vinicius Junior and Karim Benzema either side of Eder Militao’s goal resulted in a 5-2 scoreline and a humbling loss for the 2019 champions.