 Dempsey akaita mutambo wake wekutanga wechikwata chenyika musi wa17 Mbudzi 2004, panguva yemutambo weWorld Cup wakanangana neJamaica muColumbus, Ohio; kushevedzwa kwakauya mushure memwaka wake wekutanga muMajor League Soccer neNew England Revolution, kwaakanyora zvibodzwa zvinomwe uye imwe inobatsira munzira yekuzodanwa zita reMLS Rookie yeGore. Dempsey akarova chinangwa chake chekutanga chikwata chenyika musi waMay 28, 2005, panguva yemutambo wehushamwari neEngland muChicago. Chibodzwa chake chekutanga chemakwikwi chikwata chenyika chakauya mwedzi wakatevera vachipesana neCuba muSeattle panguva ye2005 CONCACAF Goridhe Mukombe, mutambo uyo United States yaizokunda. 