Bailey akasarudzwa zviri pamutemo kuti amiririre Canada kumaOlympics ezhizha ra1996 mushure mekukunda mukombe wake wechitatu wenyika mumakwikwi emamita zana. Musi waJuly 27, pashure pokutanga kwakakanganiswa zvikuru munhangemutange yacho, Bailey akakunda mukombe weOlympic 100m achiisa rekodhi yenyika itsva yemasekondi 9.84. Munguva yemakwikwi, akasvika pakumhanya kwakanyanya kwe12.10 m / s (43.6 km / h kana 27.1 mph), yaive yekumhanyisa kumhanya kwakanyanya kwakambonyorwa nemunhu panguva iyoyo. VaCanada vakawanda vakanzwa kuti kukunda kwaBailey kwakadzorera mufananidzo wevatambi veCanada, pashure pokubudiswa pachena kwenhau yaBen Johnson yokushandisa zvinodhaka. Panguva iyoyo, Bailey akanga ari munhu wechipiri chete mushure meCarl Lewis kuti agare mazita ose makuru mu100m panguva imwe chete (World Champion, Olympic Champion & World Record Holder). Mazuva matanhatu gare gare, akapedza 100m/4x100m kaviri zvakare, achisimbisa Canada kune yavo yekutanga yeOlympic 4x100m zita
munhoroondo yenyika yemasekonzi 37,69.