Backing up some good domestic success in terms of the Premier League and FA Cup, Chelsea have won the League Cup five times over the years including four times in the Premier League era.
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Chelsea League Cup Wins
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 3, 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.
2006-07 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.
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.
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.
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.
Having taken the lead in the 2008 League Cup Final it was desperately disappointing to see the Blues lose out to Tottenham, falling eventually to an extra-time goal from Jonathan Woodgate. Even closer was their defeat in the 2019 final which went all the way to penalties against Manchester City after a 0-0 draw, Pep Guardiola’s side just coming out on top in the shoot-out after a miss from Jorginho.
Chelsea lost out at the first attempt (round 3) of both the 2005/06 and 2010/11 seasons, firstly when losing to Charlton on penalties at Stamford Bridge and latterly when coming out on the wrong end of a 4-3 score line against Newcastle United.