Chelsea League Cup Titles & Results By Season

2014-2015: Chelsea 2-0 Tottenham Hotspur

In beating Tottenham 2-0 in the final at Wembley, Chelsea secured their fifth League Cup success as part of a trophy-laden double spell under the management of Jose Mourinho.

A narrow 2-1 win against Bolton got the campaign underway in round three, before successes against Shrewsbury (2-1) and Derby (3-1) led the Blues to a semi-final spot against Liverpool. Following a 1-1 draw at Anfield in the first leg, Chelsea won their place in the final at the Bridge 2-1 thanks to an extra-time goal from Branislav Ivanovic.

2006-2007: Chelsea 2-1 Arsenal

The 2006-07 campaign was an extraordinary season in which Chelsea were in the hunt for a quadruple right until May 1st. Their first trophy of two that season was secured in the League Cup Final at the Millennium Stadium in Cardiff when Didier Drogba’s double was enough to beat Arsenal 2-1.

A 4-0 success against Wycombe Wanderers in the second leg of the semi-final was enough to get Jose Mourinho’s men there following wins against Blackburn, Aston Villa and Newcastle in the earlier rounds.

2004-2005: Liverpool 2-3 (a.e.t.) Chelsea

Jose Mourinho’s first trophy as Chelsea manager was the 2005 League Cup but his team made a very tough start to the competition. A 1-0 win against West Ham kicked things off before extra-time was needed at St James’ Park against Newcastle, the Blues eventually winning 2-0 on Tyneside.

Things continued to be close; a goal two minutes from time was enough to beat Fulham 2-1 before the first leg of the semi-final was drawn 0-0 against Manchester United. An 85th minute goal at Old Trafford took Chelsea to Cardiff for the final though, where a Steven Gerrard own goal on 79 minutes took the match against Liverpool to extra-time.

Ultimately Chelsea ran out 3-2 winners in the final of what was an attritional tournament for the Blues and which epitomised their will to fight.

1997-1998: Chelsea 2-0 (a.e.t.) Middlesbrough

Having not won the trophy for some 33 years, Chelsea weren’t considered favourites for the 1998 League Cup however it proved to be a glorious campaign for them first under Ruud Gullit and ultimately under Gianluca Vialli.

Narrow wins against Blackburn, Southampton and Ipswich put the Blues into the semi-finals, where they lost the first leg at Arsenal. A stirring comeback in the tie and a 3-1 second-leg win though meant a trip to Wembley where Chelsea beat Middlesbrough after extra-time, less than a year after beating the same club in the FA Cup Final.

1964-1965: Chelsea 3-2 (agg) Leicester City

Tommy Docherty’s men had a great season in 1964-65, finishing third in the First Division and reaching the semi-finals of the FA Cup.

It was Chelsea’s first ever League Cup win though that was the highlight of a memorable year, the team beating Leicester City 3-2 over two legs in the final with all the goals coming at Stamford Bridge in the first game.

2023-2024: Chelsea 0-1 (a.e.t.) Liverpool

In the 2021-2022 season, Chelsea made it to the final but lost to Liverpool in a penalty shootout. When the two teams appeared in the final again in the 2023-2024 campaign, the hope from Stamford Bridge was that things would be different this time. Whilst the club was hoping to seek revenge, so too was the manager, with Mauricio Pochettino having lost the 2019 Champions League final to Jürgen Klopp.

Because Chelsea had no European competition to contend with, the Blues entered the League Cup in the second round, winning 2-1 against AFC Wimbledon at home. That resulted in another tie at Stamford Bridge, this time against Brighton & Home Albion, with the home side running out as 1-0 winners against the club they had paid a lot of money to for Moisés Caicedo.

A 2-0 win over Blackburn Rovers saw Chelsea make the quarter-finals, winning 4-2 on penalties against Newcastle United after a 1-1 draw in normal time. The semi-finals resulted in a shock 1-0 first-leg loss to Middlesbrough, followed by a 6-1 win at home. In the final, it was yet another tight affair with Liverpool before Virgil van Dijk headed the winner for the Merseyside club in the dying moments of extra-time.

2021-2022: Chelsea 0-0 Liverpool (10-11 pens)

The 2021-2022 League Cup final pitted Chelsea up against Liverpool in a match that would later be repeated in the FA Cup, as well as the 2023-2024 version of the League Cup Final. Chelsea had beaten Aston Villa at home in the third round match, beating them 4-3 on penalties and setting up a fourth round tie against Southampton.

That ended 1-1, meaning another penalty shootout, which the Blues won 4-3. In the quarter-finals Chelsea won 2-0 away from home against Brentford, whilst the two-legged semi-finals put the Blues up against London rivals Tottenham. Chelsea won the first-leg 2-0 and the second-leg 1-0.

The final, as would be the case in the FA Cup, was a tense affair with no goals scored. The penalty shootout, meanwhile, was brilliant, with every single player scoring and requiring the goalkeepers to take pens. Unfortunately for Chelsea, Caoimhín Kelleher scored his but then saved Kepa Arrizabalaga's.

2018-2019: Chelsea 0-0 Manchester City (3-4 pens)

The fact that Chelsea were playing in the 2018-2019 Europa League meant that their journey to Wembley began in the third round of the League Cup, which they won 2-1 against Liverpool at Anfield. Next up it was a home game against Derby County, with Chelsea winning the match 3-2, with all goals scored in the first-half.

Chelsea had to take on fellow Premier League side Bournemouth in the quarter-finals, with an Eden Hazard goal proving to be decisive. It was an all-London semi-final for Chelsea, taking on Tottenham Hotspur over two legs. Spurs won the first-leg 1-0 thanks to a Harry Kane goal, whilst N'Golo Kanté scored the aggregate equaliser at Stamford Bridge.

Goals from Hazard and Fernando Llorente meant a penalty shootout was needed, which Chelsea won 4-2. The final itself ended up being a bit disappointing, with no goals scored in either then 90 minutes nor extra-time meaning a penalty shootout was again required. Manchester City won it 4-3.

2007-2008: Chelsea 1-2 (aet) Tottenham Hotspur

It was a trip away to Hull City for Chelsea in the third round of the 2007-2008 League Cup, which the Blues won thanks to a comfortable 4-0 scoreline. That set up a match against Leicester City at Stamford Bridge in the fourth round, which was a seven goal thriller that the the London club won 4-3.

Liverpool were the visitors to Stamford Bridge in the quarter-finals, with Chelsea running out comfortable 2-0 winners over Rafael Benitez's side. Having dispatched one Merseyside club, the Blues then had to deal with the other one in the semi-final when they were drawn to play against Everton.

A 2-1 win in the first-leg and a 1-0 win in the second put Chelsea through to a final with fellow Londoners Tottenham Hotspur, who had beaten Arsenal in their semi-final matchup. Didier Drogba gave Chelsea the lead after 39 minutes, but a 70th minute penalty from Dimitar Berbatov and a 94th minute winner from Jonathan Woodgate saw the Blues on the losing side.

1971-1972: Stoke City 2-1 Chelsea

Having won the FA Cup and the UEFA Cup Winners' Cup in the previous two season, there was a sense that Chelsea were all-but destined to win the League Cup when they made the final. They defeated Plymouth Argyle in the second round to begin their journey, drawing 1-1 with Nottingham Forest in the third round.

A 2-1 win in the replay set up a match against Bolton Wanderers in the fourth round, which also ended 1-1. The replay was a one-sided affair, though, with Chelsea defeating Bolton 6-0. A 1-0 win over Norwich City in the quarter-final was enough to mean the Blues would take on Tottenham Hotspur in the semi-final.

The first-leg ended 3-2 to the Blues, with the second-leg finishing 2-2 for a 5-4 aggregate win. Stoke City were club's opponents in the final, with the Potters taking the leader after just five minutes through Gerrard Conroy. A Peter Osgood goal on the stroke of half-time brought Chelsea back into it, but George Eastham scored the winner for Stoke in the 73rd minute.