Chelsea FC’s Five Most Heartbreaking Moments

1 – John Terry’s Slip-Up (Manchester United 1-1 Chelsea (6-5 on Penalties), May 2008 )

There will be no surprises in terms of which particular moment will count as the most heartbreak inducing event in Chelsea’s history. In the club’s first Champions League final, a poacher’s finish from Frank Lampard had cancelled out Cristiano Ronaldo’s header. An eventful half-hour of extra-time saw Lampard hit the crossbar (which was not going to prove to be a very good friend to us that night) and Didier Drogba was sent off for a ridiculously light yet irresponsible slap of Nemanja Vidic’s cheek.

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When it came to penalties, and for fate to show its cruelness towards one team, nerves were at an all-time high. In recent seasons, penalty shoot-outs had tended to be Chelsea’s enemy. However, when Ronaldo’s poor penalty was diligently pushed away by Petr Cech, and our players kept slotting theirs home, it seemed Chelsea already had a hand on ‘Big Ears’. When the fifth and final penalty came up, captain John Terry took over from the dismissed Drogba. I challenge any Chelsea fan to claim that they did not picture the headlines following our ever-reliable homegrown captain scoring to give the club its first Champions League title…

Sometimes what seems like the perfect headline doesn’t come to fruition in real life. John Terry slipped, the ball hit the post, and an unfathomable nausea took over all in royal blue. In the end it was Anelka’s saved penalty which saw Manchester United lift the trophy, but whereas that moment won it for them, Terry’s slip lost it for us. The Moscow rain did little to veil Terry’s tears, and once again the Holy Grail of club football had escaped Chelsea.

On a cheerier note, and in the words of commentator Andy Gray which will forever be imprinted in Chelsea supporter’s memories as Drogba steadied himself before taking a certain penalty in 2012 : “My word, what goes around really does comes around “.