He was signed for £24m in 2004 from French club Marseille as one of Roman Abramovich's key initial signings after the Russian billionaire took over the London outfit - and Drogba can now sign off having delivered the one trophy Abramovich craved more than any other.
If anyone deserved a Champions League winner's medal it was the powerful striker - he had previously lost in one final, three semi-finals, one quarter-final and twice in the last 16.
But, on Saturday, the Ivory Coast striker scored the decisive spot-kick in the penalty shoot-out at the Allianz Arena to erase all those previous scars.
Drogba's 16 goals help Chelsea win their first top-flight title in 50 years. He also scores the winner in the League Cup final.
Becomes first Chelsea player since Kerry Dixon to reach 30 goals in a season, including two in the League Cup final win over Arsenal and the winner in the FA Cup final against Manchester United. Named African player of the year.
Expresses a desire to leave Chelsea following the departure of Jose Mourinho, but later says he regrets the comments. Becomes leading scorer in League Cup finals with goal in Chelsea's loss to Tottenham. Sent off in the Champions League final, which Chelsea lose on penalties to Man Utd.
Banned for three matches for throwing a coin into a section of Burnley fans during Carling Cup defeat. Labels referee Tom Henning Ovrebo a "disgrace" during a foul-mouthed tirade to TV cameras after his side's Champions League exit at the hands of Barcelona. Scores his sixth goal in major cup final as Chelsea beat Everton to win the FA Cup.
Wins Golden Boot for his 29 goals that help Chelsea win the Premier League.
Drogba contracts malaria, but makes full recovery. Named in Time magazine's 100 most influential people for role in peace process in Ivory Coast.
Scores his seventh goal at Wembley in FA Cup semi-final win and becomes first player to score in four FA Cup finals in win over Liverpool. Scores equaliser and winning penalty in the shoot-out as Chelsea beat Bayern Munich to win the Champions League.
Despite being a player who consistently delivered for Chelsea - he scored nine goals in nine finals - Europe's top competition always looked destined to elude him.
Drogba, though, maintained the faith.
Accused of being an "actor" by some because of his theatrics, in Munich he put in a performance more in keeping with the power and poise which made him such a feared opponent for defenders, scoring with a bullet header to equalise against Bayern before converting the crucial penalty.
The man himself put the success down to divine intervention.
"It was [fate]," said the 34-year-old. "I believe a lot in destiny. I pray a lot. It was written a long time ago. God is wonderful. This team is amazing.
"I'm very happy. Life is fantastic."
Drogba scored for Marseille on his Champions League debut in a 4-2 defeat at Real Madrid in September 2003 - 75 appearances and 39 goals later he finally had a Champions League winners' medal hanging from his neck.
It is a testament to his determination and resolve that he delivered at the end of a season which had started in such unpromising fashion.
He was a peripheral figure seemingly on his way out of Chelsea under former boss Andre Villas-Boas during the first half of the campaign but, as has so consistently been the case during his time with the Blues, he came to their rescue when the club needed him most.
"Didier Drogba has been the best centre forward of his type, certainly in the Premier League, for the past eight years," former Manchester United defender and Sunderland manager Steve Bruce told BBC Radio 5 live.
"How are they going to replace him? He has been quite fantastic, year in and year out."
While there is plenty to admire about Drogba's qualities on the pitch, it is a tribute to the 2006 and 2009 African Footballer of the Year that he uses his fame to try to
bring peace to his native Ivory Coast.
He is one of the 11 members of Ivory Coast's Truth and Reconciliation Commission and, although his team-mate Frank Lampard was talking about his value to Chelsea, he also summed up what he means to so many people far beyond the football pitch.
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