The Ivory Coast’s Didier Drogba was sent-off for a petulant slap deep into extra-time as the teams finished 1-1, and then Michael Essien (Ghana), John Mikel Obi (Nigeria), Salomon Kalou (Ivory Coast) and the DR Congo-born Claude Makalele had victory snatched from their grasp by a slip from their captain John Terry in the shoot-out.
After Ronaldo and Frank Lampard had scored in regulation time, the former missed in the shoot-out and Terry had the chance to win a first-ever Champions League title for Chelsea with the teams locked at 4-4.
But as he moved to strike the ball in the pouring rain, his standing leg appeared to go from under him and the ball speared wide. Nicolas Anelka later missed again for Chelsea as United claimed a third trophy to go with their English Premiership win this season.
Would Terry have taken the spot-kick had Drogba remained on the pitch will forever be a question that will haunt Chelsea supporters.
United were the better side in the opening 30 minutes and deservedly took the lead when Ronaldo lost his marker – Essien – and headed Owen Hargreaves’ cross into the bottom corner.
But the goal seemed to spur the Blues, and they gradually managed to find a foothold in the game, though Carlos Tevez should have made it 2-0 when he failed to make a proper connection on Wayne Rooney’s low cross with the goal gaping.
But Lampard equalised just before halftime after hesitant defending from United, when he latched onto the rebound from Makalele’s innocuous shot from 30-yards that struck a defender and bounced into his path.
And Chelsea were the better side in the second period, as both Drogba and Lampard hit the woodwork, and United failed to trouble Petr Cech in the Londoners’ goal.
But the match went to extra time, and as the pace slowed, tempers rose and Drogba was sent-off in an unsavoury incident that saw him slap the cheek of United defender Nemanja Vidic after some pushing and shoving amongst the players.
And at almost 02h00 in the morning in Moscow, the penalty shoot-out was filled with drama. As Terry stepped up to celebrate his – and his club’s – finest moment, it quickly turned to despair.