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Liverpool vs Chelsea: Five Recent Cup Clashes That Ended in Heartbreak

Nicole Powell, Manager · · 3 min read

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Liverpool vs Chelsea: Five Recent Cup Clashes That Ended in Heartbreak
RECORD DATE NOT STATED Football – Football League Cup – 4th Round – Liverpool FC v Chelsea FC LIVERPOOL, ENGLAND – Wednesday, October 28, 2026: Chelsea s goalkeeper Mike Penders makes a save from Liverpool s Ronald Araujo header during the Football League Cup 4th Round match between Liverpool FC and Chelsea FC at Anfield. (Photo by David Rawcliffe Propaganda) LIVERPOOL Anfield MERSEYSIDE ENGLAND Copyright: xDavidxRawcliffex 2026-10-28-Liverpool_Chelsea-066

Xabi Alonso’s men were kicked out of the Carabao Cup on Wednesday, October 28, after losing the Liverpool vs Chelsea fixture 6-5 on penalties following a 1-1 draw at Anfield.

Wesley Fofana missed the decisive spot-kick after both teams converted penalties during normal time, with Morgan Rogers and Cody Gakpo finding the net before the break. The result continued Liverpool’s recent dominance in cup meetings between the two sides, with the Reds also winning three major finals against Chelsea in recent years.

Here are five memorable Liverpool vs Chelsea cup clashes from the past seven years.

1. Liverpool vs Chelsea: Carabao Cup – October 2026

Wednesday’s Liverpool vs Chelsea meeting at Anfield was another tight contest between the two sides, with neither able to find a winner during normal time.

Chelsea took the lead through Rogers’ penalty before Fofana conceded a spot-kick that allowed Gakpo to equalise.

Both teams had chances to win the game, but goalkeeper Mike Penders made several important saves to keep Chelsea in the contest.

However, the Blues eventually fell short in the shootout, with Fofana’s miss allowing Liverpool to advance to the quarter-finals.

2. Chelsea vs Liverpool: Carabao Cup Final – February 2024

Liverpool beat Chelsea 1-0 after extra time to lift the Carabao Cup at Wembley in February 2024.

Both sides had goals ruled out for offside and struck the woodwork during a closely contested final, which looked set to be decided by penalties.

However, Virgil van Dijk headed home from a Konstantinos Tsimikas corner in the 118th minute to secure the trophy for Liverpool.

The Blues had chances to take the lead earlier in the Chelsea vs Liverpool game, but the Blues were unable to make the most of their opportunities.

3. Chelsea vs Liverpool: Carabao Cup Final – February 2022

The first of Liverpool’s two Wembley victories over Chelsea in 2022 was another goalless draw that went to penalties.

Both sides had goals disallowed during normal time, while Chelsea goalkeeper Edouard Mendy and Liverpool’s Caoimhin Kelleher produced important saves.

After extra time failed to separate the teams, the shootout went all the way to the goalkeepers.

Kelleher scored his penalty before Chelsea goalkeeper Kepa Arrizabalaga blazed his effort over the crossbar, handing Liverpool an 11-10 victory.

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4. Chelsea vs Liverpool: FA Cup Final – May 2022

Liverpool and Chelsea met again at Wembley less than three months later, this time in the FA Cup final.

The Chelsea vs Liverpool 2022 FA Cup final saw both teams struggling to find a breakthrough across 120 minutes.

Liverpool hit the woodwork twice late in normal time, while Chelsea also came close to scoring. Neither side could find a winner, sending the game to penalties.

Liverpool eventually won 6-5 in the shootout, with Tsimikas converting the decisive spot-kick after Alisson Becker saved Mason Mount’s effort.

The result gave Liverpool a domestic cup double after their earlier Carabao Cup triumph.

5. Liverpool vs Chelsea: Carabao Cup – September 2018

Chelsea got the better of Liverpool when the teams met at Anfield in the third round of the Carabao Cup in September 2018.

In the second half of the Liverpool vs Chelsea fixture, the hosts took the lead through Daniel Sturridge, but Emerson Palmieri equalised before substitute Eden Hazard made the difference.

The Belgian produced a brilliant solo run before firing past Simon Mignolet in the 85th minute to secure a 2-1 victory for Chelsea.

It remains a memorable result for the Blues, who ended Liverpool’s hopes of winning the competition that season.

Extra Time Notes

The Reds have had the upper hand in recent Liverpool vs Chelsea cup meetings, particularly in finals, where the smallest details have repeatedly worked in their favour.

Chelsea have pushed the Reds close on several occasions, but Wednesday’s defeat was another reminder of how difficult it has been for the Blues to get past their rivals when a trophy or progression is at stake.

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Nicole Powell, Manager

Nicole Powell is the site manager of ExtraTime Talk, a football site in the Last Word on Sports (LWOS) network. She previously managed Last Word on Motorsport. She specialises in F1 and football, and is also the lead content editor at Transfer News Blitz, sub-editor within the News Blitz and SIP Media Solutions network, as well as a women's football writer at Beyond the Pitch.

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