Nyorera kupfuurira kweiyi ndima - Kwemwaka wa2008, Wheldon akagara neCGR. Akatanga gore achipedza wechitatu mumwaka wekuvhura Gainsco Auto Inishuwarenzi Indy 300 kuHomestead <unk> Miami Speedway mushure mekufamba kuburikidza nemunda uchitanga kubva pa22nd. Wheldon akakunda RoadRunner Turbo Indy 300 paKansas Speedway makwikwi matatu gare gare, achiva mutyairi wekutanga weIndyCar kutora kukunda kaviri kwakateedzana munzira. Akatanga ari mugumi namasere muIndianapolis 500
kupedza nzvimbo nhanhatu dzakakwirira munzvimbo yegumi nembiri nemhaka yezvinetso zvokutarisira mumakumbo 50 okupedzisira. Wheldon akatora kukunda kwake kwechipiri (uye kwekupedzisira) kwemwaka muIowa Corn Indy 250 kuIowa Speedway. Akapa mubayiro wake kuti abatsire vakanga vawirwa nedutu remhepo nemafashamo akanga achangobva kuitika muIowa. Sezvo IndyCar yakanga yave yakanyanya kutarisana nemigwagwa nemigwagwa yemigwagwa, kushanda kwake kwakaderera mumakwikwi akasara. Akawana imwezve podium, nzvimbo yechipiri paNashville Speedway, uye shanu dzepamusoro-manomwe dzakapedza nzvimbo yechina mumakwikwi evatyairi vane 492 mapoinzi.