As one of the most decorated clubs in English football history, Chelsea have tasted success in every domestic and European competition at least once and are always a popular choice for punters taking advantage of the best free bets available online.
On the back of a solid start to the Premier League season, Chelsea kicks off their 2024/25 Carabao Cup campaign with a home clash against League Two outfit Barrow A.F.C. on Tuesday, 24th of September. Will this be the beginning of a journey towards Wembley and a place alongside the following five League Cup-winning sides?
1965 Final: Chelsea 3–2 Leicester City (First League Cup Win)
Chelsea’s first significant achievement in the League Cup came in 1965, under manager Tommy Docherty. The final was played over two legs against Leicester City. Chelsea won the first leg at Stamford Bridge 3–2 and then secured a 0-0 draw in the second leg at Filbert Street to win their first-ever major trophy.
Led by stars like Bobby Tambling and Peter Bonetti, Chelsea showed resilience throughout the tournament. This victory was particularly historic as it marked the club’s emergence as a competitive force in English football. Though the League Cup wasn’t yet regarded as highly as other domestic competitions, this win laid the foundation for future successes.
1998 Final: Chelsea 2–0 Middlesbrough (Gianluca Vialli’s Era)
The late 1990s marked the rise of Chelsea as a true domestic and European power. Under player-manager Gianluca Vialli, Chelsea beat Blackburn Rovers, Southampton, Ipswich Town and London rivals Arsenal en route to a clash with a Bryan Robson-led Middlesbrough in the final.
With the North East club putting up stern resistance, the Blues needed extra time to get their hands on the trophy, thanks to strikes from Frank Sinclair and Roberto Di Matteo.
2005 Final: Chelsea 3–2 Liverpool (José Mourinho’s First Trophy)
Perhaps one of the most memorable League Cup finals for Chelsea fans came in 2005 when José Mourinho led the club to victory over Liverpool. The match was a thrilling encounter that required extra time. Liverpool took the lead after one minute through John Arne Riise, but Chelsea equalized in the 79th minute, courtesy of an own goal from Steven Gerrard.
In extra time, Chelsea took control with goals from Didier Drogba and Mateja Kežman to secure a 3–2 victory. This triumph was significant because it marked José Mourinho’s first trophy in English football, setting the stage for Chelsea’s domestic dominance in the years to come. The victory also solidified the reputation of Mourinho as a master tactician and Chelsea as a force to be reckoned with in the Premier League and cup competitions.
2007 Final: Chelsea 2–1 Arsenal (Drogba’s Masterclass)
Two years after Mourinho’s first League Cup triumph, Chelsea once again reached the final in 2007 – this time facing a young Arsenal side brimming with talent. Arsenal took the lead early in the game through Theo Walcott, but Didier Drogba, who had developed a reputation for stepping up in big moments, equalized soon after with a smart finish from inside the area.
The match looked destined for extra time, but Drogba struck again late in the second half, scoring the winner with a trademark header. This 2–1 victory gave Chelsea their fourth League Cup trophy and reinforced the club’s winning mentality under Mourinho.
2015 Final: Chelsea 2–0 Tottenham Hotspur (Mourinho’s Return)
In 2015, José Mourinho was back at Chelsea for his second stint, and he once again guided the club to League Cup success. In the final, Chelsea faced their London rivals Tottenham Hotspur, a team that had beaten them 5-3 in the Premier League earlier in the season.
However, the final was a completely different affair, with Chelsea delivering a controlled and clinical performance. John Terry scored the opener just before halftime, and a Kyle Walker own goal in the second half secured a 2–0 victory for Chelsea. This win was significant as it was Mourinho’s first trophy during his second tenure at the club and set the tone for Chelsea’s Premier League title win later that season.
