CARDIFF, UNITED KINGDOM – FEBRUARY 25: Chelsea Manager Jose Mourinho celebrates with the trophy following his team’s victory at the end of the Carling Cup Final match between Chelsea and Arsenal at the Millennium Stadium on February 25, 2007 in Cardiff, Wales. (Photo by Alex Livesey/Getty Images)

Chelsea’s history in the Capital One Cup Final

Both Chelsea and Tottenham have had long and storied histories in the Capital One Cup. Both teams have had their share of wins and losses in the Final. We will cover Tottenham’s history later today but for now, we’re talking about Chelsea and how they have performed in this tournament.


1965-Chelsea 3-2 Leicester City

Chelsea’s first League Cup win came in the fifth Final against Leicester City. This was still in the time that League Cup Finals were played over home and home two leg series. Chelsea got to host at Stamford Bridge for the first leg.

This game went back and forth but Chelsea always had the upper hand. When Chelsea would score, Leicester City would equalize. When Chelsea scored again, Leicester City equalized again. Once it was 2-2, Chelsea scored again thanks to an Eddie McCreadie goal late in the game that sealed the game for Chelsea. A 0-0 draw in the second leg a couple weeks later cemented Chelsea’s first win in the League Cup.


1972-Chelsea 1-2 Stoke

Chelsea’s first loss in the League Cup Final came at the hands of Stoke. Chelsea was on the complete opposite end of the scoring when compared to their first Final against Leicester. Stoke scored early and then Chelsea equalized. Towards the end of the game, Stoke’s George Eastham scored the game winner and gave Stoke their only major trophy in their 152 year history.


1998-Chelsea 2-0 Middlesbrough

Chelsea and Middlesbrough kept things tight throughout the first 90 minutes. In fact, it was so tight that after 90 minutes, the score was 0-0. Going into the extra time period, it was anybody’s game.

Things very quickly went into Chelsea’s favor in extra time. Frank Sinclair and Roberto di Matteo scored very quickly into extra time. While it took them 33 years, Chelsea finally got their second title.


2005-Chelsea 3-2 Liverpool

Chelsea’s third League Cup win also was decided in extra time. John Arne Riise started the scoring right away by scoring a brilliant goal within 45 seconds and securing a League Cup Final record for the fastest goal in a Final.

The game was going all Liverpool’s way and then Steven Gerrard had one of his “not so finer” moments as a soccer player. He headed in a long Chelsea pass and granted Chelsea with their equalizer.

Chelsea took the extra time period to their advantage. By scoring twice in five minutes, it was all but over for Liverpool. Even though Liverpool scored, they could not make up the third goal and Jose Mourinho celebrated his first trophy as Chelsea manager.


2007-Chelsea 2-1 Arsenal

Jose Mourinho came back with Chelsea and led Chelsea to their fourth and final League Cup. Theo Walcott started the scoring by scoring his first goal as an Arsenal player. Chelsea soon scored the equalizer thanks to Didier Drogba and he scored again in the 84th minute to win the trophy for Chelsea.


2008-Chelsea 1-2 Tottenham Hotspur

The two teams that will face off Sunday last played in the League Cup Final in 2008. Though Chelsea was in the League Cup Final last year, they entered this Final without manager Jose Mourinho. He left to go to Inter and Avram Grant led the way for Chelsea as manager.

Just like the Chelsea team in 2007, Didier Drogba was the lone goalscorer for Chelsea. Unfortunately for Drogba and Chelsea, one goal wasn’t enough. After a handball, Tottenham converted the PK to equalize. Then in the last few seconds of the game, a fortunate bounce off of Jonathan Woodgate won the title for Tottenham. Will the same thing happen on Sunday? We’ll just have to find out at 11 AM ET Sunday on beIN Sport.

About Phillip Bupp

Producer/editor of the Awful Announcing Podcast and Short and to the Point. News editor for The Comeback and Awful Announcing. Highlight consultant for Major League Soccer as well as a freelance writer for hire. Opinions are my own but feel free to agree with them. Follow me on Twitter and Instagram @phillipbupp