Xabi Alonso Returns to Anfield as Chelsea Face Liverpool in Carabao Cup Clash

Former Liverpool midfielder Xabi Alonso returns to Anfield on Wednesday evening, this time in the opposition dugout as his Chelsea side take on Liverpool in the fourth round of the Carabao Cup.

The Spaniard, who spent five successful seasons on Merseyside between 2004 and 2009, will be hoping to guide Chelsea into the quarter-finals when they face Andoni Iraola’s Liverpool at 8:00pm.

It promises to be an intriguing occasion for both clubs, with Liverpool looking to extend their four-match winning run in all competitions, while Chelsea are seeking an immediate response following their disappointing 2-0 Premier League defeat against Tottenham Hotspur on Saturday.

The contest will also see two managers who have known each other since childhood go head-to-head, with Alonso and Iraola having grown up together in Spain’s Basque Country.

Xabi Alonso’s Liverpool Career and Return to Anfield

Alonso remains a popular figure among Liverpool supporters following an impressive five-year spell at the club under Rafael Benitez.

Arriving from Real Sociedad in 2004, the Spanish international quickly established himself as an important member of Liverpool’s midfield, combining excellent passing ability with an impressive understanding of the game.

He played a crucial role in Liverpool’s unforgettable 2004/05 Champions League triumph, scoring the equaliser against AC Milan during the remarkable comeback in Istanbul. Alonso also helped the Reds win the FA Cup in 2006 before departing for Real Madrid three years later.

Following his retirement from playing, Alonso established himself as one of Europe’s most highly regarded young managers.

His most significant achievement came during the 2023/24 campaign, when he guided Bayer Leverkusen to their first Bundesliga title, completing an unbeaten domestic league season and securing the German Cup.

A subsequent spell in charge of Real Madrid ended in January 2026, before Chelsea appointed him as their new manager ahead of the current campaign.

Wednesday will not be Alonso’s first return to Anfield as an opposing manager. His Bayer Leverkusen side suffered a 4-0 Champions League defeat against Liverpool in November 2024, while he also oversaw Real Madrid’s 1-0 loss at the stadium in November 2025.

However, this occasion carries additional significance, with Alonso now managing one of Liverpool’s biggest domestic rivals.

The Chelsea boss has made his position clear ahead of the encounter, insisting that his responsibility is to his current club and confirming that he would celebrate a Chelsea goal, while maintaining his respect for Liverpool.

Childhood Friends Alonso and Iraola Go Head-to-Head

Another interesting aspect of Wednesday’s encounter is the relationship between Alonso and Liverpool manager Andoni Iraola.

The pair have known each other since childhood, having grown up in the Basque province of Gipuzkoa before enjoying successful playing careers.

Both went on to represent Spain, with Alonso establishing himself as a regular member of the national side that won the 2008 European Championship, 2010 World Cup and 2012 European Championship.

Their managerial careers have since brought them to two of English football’s biggest clubs, setting up a competitive meeting at Anfield.

Iraola discussed their longstanding friendship during his pre-match press conference, explaining that their personal relationship would be put aside for the duration of Wednesday’s encounter.

The Liverpool manager will be determined to continue his side’s recent improvement, while Alonso has the opportunity to secure an important victory over his former club.

Liverpool Looking to Extend Winning Run Ahead of Arsenal Clash

Liverpool enter Wednesday’s fixture in encouraging form after securing four consecutive victories across all competitions.

Their most recent success came on Sunday afternoon, when they defeated Brighton & Hove Albion 2-0 at Anfield to climb to fourth in the Premier League table.

A Pascal Gross own goal opened the scoring after Florian Wirtz’s effort was deflected into the net, before Alexander Isak doubled Liverpool’s advantage just four minutes later.

The Swedish international has enjoyed an impressive start to the campaign, scoring six Premier League goals, including strikes in each of his last three league appearances.

Liverpool also recorded a 4-3 Champions League victory over Villarreal last week, demonstrating their growing confidence in front of goal.

However, Iraola faces several selection decisions ahead of the Carabao Cup fixture.

Florian Wirtz is expected to be available despite suffering an ankle injury against Brighton, although Dominik Szoboszlai and Victor Munoz remain doubts. Conor Bradley, Jeremie Frimpong, Hugo Ekitike and Giovanni Leoni are also unavailable.

Iraola has already confirmed that he intends to rotate his squad, with Liverpool preparing for Sunday’s important Premier League encounter against Arsenal at Anfield.

The likes of Rio Ngumoha, Trey Nyoni and Lewis Koumas could therefore be handed opportunities as the Reds look to progress in the competition.

Chelsea Seeking Response Following Tottenham Defeat

Chelsea travel to Merseyside following a disappointing weekend in which they suffered a 2-0 home defeat against Tottenham Hotspur.

Roberto De Zerbi’s side secured their first victory at Stamford Bridge since 2018, leaving Alonso with plenty to consider ahead of Wednesday’s cup encounter.

Chelsea have already defeated Luton Town and Leeds United in this season’s Carabao Cup, but face a considerably more difficult challenge against an improving Liverpool side.

Their preparations have also been complicated by the absence of several important players.

Cole Palmer will miss the fixture through suspension after receiving a red card against Tottenham, while Brazilian forward Joao Pedro has been ruled out for several weeks with a thigh injury.

However, Alonso has confirmed that summer signing Emmanuel Emegha could make his Chelsea debut after recovering from a hamstring problem.

The Dutch international has been building his fitness in recent weeks and could provide Chelsea with another attacking option. Estevao and Danny Welbeck are also available for selection.

Another former Liverpool player who could feature is Jordan Henderson, who will also be returning to Anfield as a Chelsea player.

The experienced midfielder captained Liverpool to Premier League and Champions League success during his time on Merseyside and could feature against his former club.

With Chelsea also preparing to face Manchester United in the Premier League this weekend, Alonso must balance his desire to progress in the Carabao Cup with the demands of the domestic season.

Liverpool and Chelsea’s Carabao Cup History

Liverpool and Chelsea have developed a considerable rivalry in domestic cup competitions, with the two clubs meeting in three League Cup finals since 2005.

Chelsea emerged victorious in their first final encounter, defeating Liverpool 3-2 after extra time in February 2005 under Jose Mourinho.

However, Liverpool have enjoyed the better of their two most recent meetings in the competition’s final.

The Reds lifted the trophy in 2022 following an extraordinary penalty shootout victory, winning 11-10 after the match finished goalless.

Two years later, Virgil van Dijk scored an extra-time winner to secure a 1-0 victory over Chelsea at Wembley, delivering Liverpool’s record-extending tenth League Cup title.

The clubs’ most recent meeting at Anfield came in May 2026, when they played out a 1-1 draw in the Premier League.

Liverpool will be hoping to continue their strong record against Chelsea in the competition, while Alonso has an opportunity to secure a memorable victory on his latest return to Merseyside.

With a place in the quarter-finals at stake, Wednesday’s encounter presents both managers with an opportunity to move a step closer to winning their first trophy with their respective clubs.

Liverpool v Chelsea Carabao Cup FAQs

When is Liverpool v Chelsea in the Carabao Cup?

Liverpool face Chelsea on Wednesday 28th October 2026, with kick-off scheduled for 8:00pm at Anfield.

Is Xabi Alonso the Chelsea manager?

Yes, Xabi Alonso was appointed Chelsea manager in May 2026 and officially took charge on 1st July 2026. He previously managed Bayer Leverkusen and Real Madrid.

Where can I watch Liverpool v Chelsea?

The Carabao Cup fourth-round clash will be broadcast live in the UK on ITV and Sky Sports, with kick-off at 8:00pm.

Who won the last Liverpool v Chelsea Carabao Cup match?

Liverpool won the clubs’ previous Carabao Cup meeting in February 2024, defeating Chelsea 1-0 after extra time in the final at Wembley Stadium thanks to a Virgil van Dijk header.