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Carabao Cup

The famous five: Chelsea’s League Cup triumphs

Will the Blues make it a sixth League Cup success this year?

24 February 2022

This year’s Carabao Cup 2022 Finalists Chelsea are no strangers to a big occasion and this competition is no different. The Blues have triumphed in the League Cup Final not once, twice, three or even four times – the West Londoners have lifted the trophy a total of five times over the course of the last 50 years.

This year, Thomas Tuchel’s side will compete for the silverware for a sixth time but it’s important to respect history and the current Blues side could learn a thing or two from their predecessors.

1965: London’s calling the League Cup

The competition was in its infancy when Chelsea became the first London team to lift the League Cup in 1965. And it was no easy ride, beating three of the four previous silverware holders along the way. The Blues saw off Birmingham City and Aston Villa in their bid to reach the coveted Final but reigning champions Leicester City awaited in the last hurdle over two legs.

It was the first leg at Stamford Bridge that saw all the excitement; the Foxes came from behind twice to level the playing field, but full-back Eddie McCreadie – an unlikely hero deployed as a makeshift striker – struck with 10 minutes left on the watch with a spectacular solo strike to hand the Blues the advantage heading into the second leg. Tommy Dochety’s Chelsea held on for a goalless draw in the return fixture at Filbert Street to secure the League Cup, giving the West Londoners a taste for triumph and setting the Blues on the path for future successes.

Also on the score-sheet was a young Terry Venables, who donned the armband for the two-legged Final. The then-Blues boss made use of a number of upcoming starlets at his disposal – much like the way that the competition is used as a platform to give rise to the next generation in the current format. Docherty’s 1965 League Cup-winning team were truly visionaries.

Chelsea 3-2 Leicester City

(First leg)

Tambling 33’, Venables 70’, McCreadie 81’

Leicester City 0-0 Chelsea

(Second leg)

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1998: Reclaiming the title

Much changed in the 33 years since Chelsea last had sight of the League Cup; the closest the Blues came to reclaiming the silverware was in 1972, when they came runners-up to Stoke City.

The arrival of Gianluca Vialli in West London less than a week before the second leg of the League Cup Semi-Final against Arsenal marked the beginning of a new era for the Club, and it’s safe to say the former Blues star, who called time on his playing career at Chelsea, was thrown in at the deep end. But the Italian took it in his stride, and – with the Blues trailing the Gunners 2-1 heading into the showdown – engineered a 4-3 aggregate victory over their London rivals to book Chelsea’s place in the Final.

Middlesbrough were the opponents this time, beating Liverpool en-route to the Final across two Semi-Final legs. And although Boro and the Blues couldn’t be separated in 90 minutes, extra-time goals from Frank Sinclair and Robert Di Matteo saw Chelsea become two-time League Cup winners.

Chelsea 2-0 Middlesbrough

Sinclair 95’, Di Matteo 107’

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2005: Mourinho makes his mark

This time, it was a change of scenery for Chelsea, as the Millennium Stadium played host to the 2005 Final, whilst Wembley Stadium was under reconstruction. And the Blues found the Welsh capital to be a happy stomping ground, edging Liverpool seven years after their last League Cup triumph.

As for boss Jose Mourinho, it represented a managerial milestone. The 2005 League Cup success marked his first trophy in the Cabinet at Stamford Bridge and it wouln’t be his last, either.

It didn’t look like it would be Chelsea’s day, falling behind within less than a minute, when John Arne Riise handed Liverpool the lead after 45 seconds. However, an own goal from Steven Gerrard took yet another League Cup Final to extra time and the Blues settled the matter with an additional 30 minutes, as Didier Drogba and Mateja Kežman turned it around. Antonio Núñez’s extra-time strike set the showdown up for a tense finale, but it was nothing more than a consolation as Chelsea ran out 3-2 victors. 

Liverpool 2-3 Chelsea

Own goal 79’, Drogba 107’, Kežman 112’

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2007: Return to the Welsh capital

Two short years later, the Blues would return to South Wales for the last League Cup Final to be played at the country’s national stadium.

Scoring in League Cup Finals became something of a habit for Drogba, who notched a brace against Arsenal in the 2007 showdown, whilst the Blues also became specialists in coming from behind in the competition, after Theo Walcott opened the scoring in the first-half, before the West Londoners summoned another fightback.

Nevertheless, there were some positives to note for Arsene Wenger’s side, as a 17-year-old Walcott introduced himself to the Gunners faithful, scoring his first professional goal in the Final. 

Chelsea 2-1 Arsenal

Drogba 20’, 84’

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2015: Déjà vu

History repeated itself when Jose Mourinho’s Chelsea side faced this year’s Semi-Finalists Tottenham Hotspur in the 2015 Final. The former Blues boss made the League Cup his first conquest to mark the beginning of his second spell in charge at Stamford Bridge – and his third with Chelsea in total.

After overcoming Liverpool in the Semi-Final, the Blues cruised to a 2-0 win over Spurs under the Wembley arch. Chelsea struck either side of the break, courtesy of skipper John Terry and leading marksman Diego Costa, and seal a fifth League Cup triumph – their latest in the competition to date.

That might have been the last time that the West Londoners lifted the trophy, but Chelsea came close in 2019, when they competed against Manchester City for the League Cup, but it was the Cityzens who made it a second successive title, marking the start of their dominance in the competition.

Chelsea 2-0 Tottenham Hotspur

Terry 45’, Costa 56’

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