Serial bridesmaids Chelsea and Pochettino need FA Cup success more desperately than anyone else

Steven Chicken
Scenes of dejection for Chelsea after their 2024 League Cup final defeat and Mauricio Pochettino with Tottenham
Chelsea have lost their last six Wembley cup finals, while Mauricio Pochettino remains trophyless in England

Since Roman Abramovich sold up at Stamford Bridge in 2022, the cupboard has been bare for Chelsea. 

That is not a very long time at all, even if the silliness of the Todd Boehly era seems to have lasted far longer, perhaps thanks to the time-dilating effects of living through the covid pandemic. But for Chelsea, it is practically a lifetime.

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Chelsea have not gone two seasons in a row without a trophy since Jesper Gronkjaer, Marcel Desailly and Mario Melchiot were first-team regulars. In other words: they never went more than a single season without some kind of silverware under Abramovich’s control.

Having lost the League Cup final to Liverpool in February, the FA Cup is now Chelsea’s last remaining hope of keeping that run alive, even if we have to be slightly generous by counting 2021/22’s European Super Cup and Club World Cup triumphs in saying it hasn’t happened already.

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If they fail in that endeavour, it would be a particular sore spot for Mauricio Pochettino, English football’s perennial bridesmaid, with two League Cup runners-up medals and a Champions League silver in his collection alongside a complete absence of English gold to sit alongside his French collection.

When Ruud Gullit’s Chelsea won the FA Cup in 1997, it marked the beginning of a new era of success that was kicked into hyperdrive by Abramovich’s billions a few years later: they added a League Cup, a Cup Winners’ Cup and another FA Cup trophy in the interim. For context, the last time they had won anything more significant than the Zenith Data Systems Cup had been in 1971.

These days, of course, winning the FA Cup is no predictor of future success. Liverpool won it in 2022 before having their worst season for seven years. Leicester City won it in 2021 and were relegated two seasons later. Manchester United claimed the trophy in 2016, and have only got worse from there. The less said about Wigan (2013) and Portsmouth (2008), the better.

Chelsea’s trophy dry spell is dangerous habit they have to break

There is nothing novel in the observation that Chelsea are a shadow of the side they were before being overtaken by Jurgen Klopp’s Liverpool and Pep Guardiola’s Manchester City in the late 2010s, with their 2019 Europa League and 2021 Champions League triumphs papering over the cracks of a side in decline. You only need to look at the Premier League table this year and last to see that.

But Chelsea are getting hungry now, with their lust for tasty gold only exacerbated by their tendency to fall short at the last hurdle over the past five years. They have come away from their past six Wembley cup finals with unwanted silver clasped in their disappointed hands.

More than any of the other semi-finalists, then, Chelsea need the FA Cup this year. At this stage, it is a relative bauble to Manchester City, even after their Champions League exit. For Manchester United, the Cup would be lovely, but their hopes and dreams are much more firmly pinned on what the new ownership can do off the pitch this summer. Just making it this far is a memorable accomplishment for Coventry City.

But Chelsea…they need this, even if just to remind themselves what that winning feeling is like. Because once you’re out of the habit of having anything to celebrate, it only puts up an even bigger barrier to success in place for the following year.