Ku sii wad qodobkan - Xilli ciyaareedkii 2008, Wheldon wuxuu la sii joogay CGR. Wuxuu bilaabay sanadka isagoo dhammeystiray kaalinta saddexaad ee xilli-ciyaareedka furitaanka Gainsco Auto Insurance Indy 300 ee Homestead <unk> Miami Speedway ka dib markii uu ka soo gudbay garoonka isagoo ka bilaabay 22-aad. Wheldon wuxuu ku guuleystey RoadRunner Turbo Indy 300 ee Kansas Speedway seddex tartan ka dib, isagoo noqday IndyCar-kii ugu horreeyay ee ku guuleysta laba guul oo isku xigta wadada. Wuxuu bilaabay kaalinta 18aad ee Indianapolis 500
isagoo dhameystay lixda boos ee ugu sareysa kaalinta 12aad sababo la xiriira dhibaatooyin la xariira 50kii wareeg ee ugu dambeeyay. Wheldon wuxuu qaatay guushiisii labaad (iyo tii ugu dambeysay) ee xilli ciyaareedkan ee Iowa Corn Indy 250 ee Iowa Speedway. Wuxuu lacagtii uu ku guuleystay ugu deeqay in uu ku caawiyo dhibanayaasha duufaantii iyo fatahaadii dhawaan ka dhacday Iowa. Maaddaama IndyCar ay u jihaysan tahay waddooyinka iyo waddooyinka waddooyinka, waxqabadkiisa ayaa hoos u dhacay tartamada haray. Wuxuu gaadhay hal boos oo kale oo abaalmarinta ah, oo ah kaalinta labaad ee Nashville Speedway, iyo shan toddobaad oo ugu sarreeya kaalinta afaraad ee horyaalka wadayaasha oo leh 492 dhibcood.