 Kunyora kuenderera mberi kweiyi ndima - Pakagadzwa kwenguva pfupi kwaGuus Hiddink kutanga kwaKukadzi zvichitevera kudzingwa kwaScolari, Drogba akafadzwa nekuvandudzwa kwemarudzi, achidzokera kuchimiro chake chekurova zvibodzwa zvine zvibodzwa zvina mumitambo mishanu mushure mekunge maneja mutsva atora. Kumutsiridzwa kwake kwakamuona achihwina zvibodzwa kaviri achipesana neBolton Wanderers, uye kanokwana kana mumitambo mina yeChampions League, imwe mumutambo wega wega wegumi nematanhatu ekupedzisira uye kota-fainari yemakwikwi achipesana neJuventus neLiverpool zvichiteerana, nezvibodzwa izvi zvichiona kuti Chelsea ipinde muma semi fainari. Mazuva mana chete mushure memitambo yake yeChampions League, Drogba akarova zvibodzwa mumutambo weFA Cup semi-fainari vachipesana neArsenal mushure mekunge Frank Lampard apasa Drogba uye akanyatsotenderedza muchengeti weArsenal Łukasz Fabiański asati apasa bhora mumambure asina chinhu eArsenal. Drogba akakonzerawo gakava mushure mekukundwa kweChelsea muChampions League semi-fainari mumaoko eBarcelona. Achinzwa kuti zvisarudzo zvakawanda zvakanga zvaenda zvinopesana neChelsea, Drogba akatsiviwa akatarisana nemutongi Tom Henning Øvrebø mushure mekuridza muridzo wekupedzisira. Akagamuchira kadhi yero mukuita uye akarekodhwa achidanidzira kuti Inyadzi chaiyo muvhidhiyo yeterevhizheni. Musi wa 17 Chikumi 2009, UEFA yakazomupa chirango chemitambo mitanhatu yeEuropean nemitambo miviri yekupedzisira yakamiswa. Kurambidzwa kwacho kwakazoderedzwa nomutambo mumwe pashure pokunge Chelsea yaita chikumbiro. Mumakwikwi eFA Cup a2009, Drogba akarova chinangwa chekutanga cheChelsea uye akaenzanisa sezvo vakaenderera mberi kuhwina 21. Ichi chakanga chiri chinangwa chake chechitanhatu mumutambo mukuru wokupedzisira muEngland. Kunyange zvazvo Drogba akanga amboratidza chido chake chekuchinja makirabhu, akasarudza kuramba aine Blues pasi pemurairidzi mutsva Carlo Ancelotti uye akasaina kondirakiti itsva. 