Feature10 past cup showdowns between Chelsea and Liverpool

Having seen off Leicester City, AFC Bournemouth, West Ham United and Fulham in the competition so far this season, Jürgen Klopp’s side will now renew a familiar rivalry.

The Reds and the Blues have enjoyed many memorable encounters in cup competitions down the years. Here are 10 of the best…

March 1965: Liverpool 2-0 Chelsea (FA Cup semi-final)

Liverpool were still seeking their first ever FA Cup triumph when they faced off against Tommy Docherty’s Chelsea at Villa Park in front of a crowd of more than 67,000.

The Londoners were a respected side, containing the likes of Terry Venables, George Graham and Ron Harris, but it was Bill Shankly’s men who prevailed, taking the lead through Peter Thompson in the second half before Willie Stevenson’s penalty wrapped up the win.

The Reds would go on to beat Leeds United at Wembley, making history in the process.

January 1997: Chelsea 4-2 Liverpool (FA Cup fourth round)

Liverpool looked to be cruising to victory at Stamford Bridge when Robbie Fowler and Stan Collymore fired them into a 2-0 lead within the first 21 minutes.

But the introduction of Mark Hughes at half-time changed things dramatically. The Welshman pulled a goal back within five minutes and Gianfranco Zola then netted an equaliser.

With Liverpool reeling, Gianluca Vialli netted twice in the final half-hour to dump Roy Evans’ side out.

February 2005: Chelsea 3-2 Liverpool (League Cup final)

Jose Mourinho’s first trophy in English football came against Liverpool after a dramatic League Cup final in Cardiff.

The Reds led for much of the game, John Arne Riise spectacularly volleying Rafael Benitez’s side in front, but an unfortunate own goal from skipper Steven Gerrard sent the game into extra-time.

Didier Drogba bundled Chelsea ahead and Mateja Kezman added a third. Antonio Nunez grabbed a subsequent consolation – his one and only goal for the club – but it was to prove in vain.

May 2005: Liverpool 1-0 Chelsea (Champions League semi-final, second leg)

One of the great Anfield nights.

Liverpool arrived into the game buoyed by a spirited goalless draw in the first leg at Stamford Bridge, and knowing they could count on a fervent home atmosphere.

Amid frenzied scenes, Luis Garcia squeezed home an opening goal inside the first four minutes, and Benitez’s side battled superbly to protect their lead thereafter, against an opponent that had cruised to the Premier League title only a few days earlier.

The rest, of course, is history, with Liverpool defeating AC Milan in Istanbul, in perhaps the greatest Champions League final of all time.

April 2006: Liverpool 2-1 Chelsea (FA Cup semi-final)

Another FA Cup semi-final, another Liverpool victory.

This one came at Old Trafford, and against a side that was cruising to another Premier League title under Mourinho. Riise opened the scoring, squeezing a free-kick home in the first half, and Garcia’s spectacular strike doubled the Reds’ lead after half-time.

Drogba pulled one back to set up a nervy finale, but Benitez’s team were able to hold on, and would go on to defeat West Ham United on penalties in the final.

May 2007: Liverpool 1-0 Chelsea [4-1 on penalties] (Champions League semi-final, second leg)

Two years after that first European epic at Anfield came another, and with the same outcome.

Liverpool trailed 1-0 from the first leg this time, but Daniel Agger’s superbly-worked goal levelled the tie on aggregate.

Both sides had chances to win the game thereafter, but in the end it would take a penalty shootout to settle matters.

As it transpired, Liverpool would score all four of their spot-kicks, with Pepe Reina saving from both Arjen Robben and Geremi, allowing Dirk Kuyt to send the Reds through to a second Champions League final in three seasons.

April 2008: Chelsea 3-2 Liverpool [4-3 on aggregate] (Champions League semi-final, second leg)

Incredibly, Liverpool and Chelsea would meet each other in the Champions League in five successive seasons between 2005 and 2009, including three times in the semi-finals.

The last of that trilogy came in 2008 when, after a 1-1 draw in the first leg at Anfield, the sides played out a thrilling return fixture.

Drogba fired Chelsea ahead on the night, but Fernando Torres’ second-half effort forced extra-time.

Frank Lampard’s penalty and another Drogba strike put Chelsea in control, but Ryan Babel’s 30-yarder kept Liverpool in the hunt until the end.

They were unable to force an away-goals winner, though, meaning it was Chelsea who progressed to face Manchester United in the final in Moscow.

May 2012: Chelsea 2-1 Liverpool (FA Cup final)

Having edged past Cardiff City in the League Cup final, Liverpool were looking to land a domestic cup double when they met Roberto Di Matteo’s Chelsea at Wembley.

But they started poorly, with Ramires firing Chelsea into an early lead before Drogba, so often the Reds’ nemesis, added a second after half-time.

Substitute Andy Carroll pulled one back, however, and was denied an equaliser only by a stunning Petr Cech save as Liverpool finished the game strongly.

Chelsea would hold on to claim the trophy, however.

February 2022: Liverpool 0-0 Chelsea [11-10 on penalties] (League Cup final)

A remarkable goalless draw, followed by an even more remarkable penalty shootout.

Quite how this game finished 0-0 is anyone’s guess, with Joel Matip seeing a goal ruled out and goalkeepers Edouard Mendy and Caoimhin Kelleher making a string of fine saves.

And the drama continued into the shootout, with 21 successful spot-kicks in a row, the last of which was scored by Kelleher, followed by Kepa Arrizabalaga, Chelsea’s substitute ’keeper, sending his effort over the bar, handing Liverpool the win.

May 2022, Liverpool 0-0 Chelsea [6-5 on penalties] (FA Cup final)

The most recent of the teams’ cup meetings came in May 2022, and ended in yet another nervy penalty shootout.

Both sides had chances to win the game in 90 minutes, and again in extra-time, but after two hours of scoreless football it came down to spot-kicks once more.

After Cesar Azpilicueta’s miss, Sadio Mane had the chance to win it for Liverpool, but saw his effort saved by international teammate Mendy.

Alisson Becker denied Mason Mount, though, allowing Kostas Tsimikas to step up and spark wild scenes of celebration among Reds fans.