The last couple of years have been a gloomy point in Chelsea’s recent history. Ever since lifting the UEFA Champions League for the second time in the club’s history back in 2021, the sky has been rather gloomy over Stamford Bridge. Last season was their worst campaign in almost 20 years, finishing way down in 12th in the Premier League table and suffering a humiliating exit on the continental stage courtesy of a comprehensive defeat by Real Madrid.

Things haven’t looked any better this season, despite owner Todd Boehly piling more than £1bn on new signings. However, in recent weeks, things have come to fruition. One of those new signings – talented young Englishman Cole Palmer – has led the revolution. They have won their last two league games on the bounce against newly promoted Luton Town and Crystal Palace however, it was in the FA Cup that they truly made a statement,

Goals from Armando Broja, Thiago Silva, Raheem Sterling and Enzo Fernandez sealed a 4-0 victory against second-tier outfit Preston North End at the Bridge. And with it, the competition may well represent the Blues’ best shot at winning a trophy this season. The bookies certainly seem to think so, with pre-match and live sports betting odds installing them as +900 second favorites. The West London side has plenty of pedigree in the esteemed tournament, and here are the last five times they tasted victory in it.

2006-07: Chelsea 1-0 Manchester United

There’s nothing quite like a 116th-minute winner – just ask Didier Drogba, who fired home the only goal of the game deep into extra time against rivals Manchester United in the 2007 final. Despite being the game – which was the first ever at the newly built Wembley Stadium – dominated by the Red Devils, the Blues’ resilience and their big Ivorian striker’s heroics secured their second piece of domestic silverware that season after also knocking off Arsenal at the Millennium Stadium to win the League Cup.

Over the previous two years, Jose Mourinho had led the club to back-to-back Premier League titles. However, Sir Alex Ferguson and United would stop them from completing a historic threepeat, while Liverpool would once again knock them out of the UEFA Champions League at the semifinal stage, just as they did two years prior.

2008-09: Chelsea 2-1 Everton

If you want to win a final, do it in style. Chelsea did just that in 2009, with goals from Drogba – ever the man for the big occasion – as well as yet another Frank Lampard stunner securing a 2-1 triumph over Everton. Even more impressive was the fact that it was Guus Hiddink who was installed as Chelsea’s manager on an interim basis, and he had already begun to make an impact that would catapult the Blues up the Premier League table.

More heartache would await on the continental stage, however. The club lost the previous year’s Champions League final – once again being pipped by Old Trafford’s finest – on penalties in Moscow. This time around, they were eliminated most controversially by Barcelona in the semifinals, being denied no fewer than four clear penalties which allowed the Catalonians to steal a last-gasp winner through Andres Iniesta.

2009-10: Chelsea 1-0 Portsmouth

The FA Cup final is always a big occasion, but for Portsmouth – who were facing the financial and operational turmoil that would later force them into administration – it was a chance to lift spirits and give their devoted fans something to cheer about. And it looked as though the impossible might be on for the Premier League’s rock-bottom club when they were awarded a second-half penalty.

However, it wasn’t to be. Kevin Prince-Boateng’s spot kick was saved allowing a Didier Drogba free-kick to seal a 1-0 victory for Chelsea in a game that was admittedly a rather gloomy affair. Pompy would ultimately be relegated at the end of the season while the Blues completed a famous double, also winning the Premier League under Carlo Ancelotti.

2011-12: Chelsea 2-1 Liverpool

If you’re a Chelsea fan, you know that there’s nothing quite as satisfying as beating Liverpool. And when it happens in an FA Cup final, it’s all the sweeter. Goals from Ramires and Didier Drogba, alongside a stunning performance from Petr Cech, ensured that it was a day for the Blues to remember.

What made it even more special was that the victory came amidst a difficult campaign for Chelsea, who were struggling in the Premier League. But they would still go on to top their Wembley heroics a fortnight later, stunning Bayern Munich in the Allianz Arena on penalties to lift the Champions League for the first time in the club’s history.

2017-18: Chelsea 1-0 Manchester United

History does repeat itself, and Chelsea proved that in the 2018 final against – you guessed it – Manchester United. A solitary Eden Hazard penalty was enough to see off the Red Devils – who were managed by former Blues boss Jose Mourinho – on a sunny afternoon at Wembley, with the Blues trading in the explosive thrills of earlier finals for a more pragmatic, cautious approach.