 Nyorai kuenderera mberi kweiyi ndima - Babayaro akasainwa neChelsea mushure mekunge aonekwa ne scout Lewis Durkin muna Kubvumbi 1997. Akatamira kune imwe nzvimbo ye 2.25 mamiriyoni, rekodhi yekambani yakabhadharwa kune wechidiki panguva iyoyo. Akaita kutanga kwake muEFAFA Cup Winners Cup kurwisa Slovan Bratislava, asi kukuvara kwakagadziriswa mukukunda 6-1 pamusoro pevakwikwidzi Tottenham Hotspur muna Zvita 1997 kwakamubvisa kwemwaka wese. Izvi zvaireva kuti akarasikirwa nekukunda kwavo mu1998 Football League Cup Final uye 1998 UEFA Cup Winners Cup Final. Zvisinei, naChelsea akaenderera mberi kuhwina 1998 UEFA Super Cup, iyo FA Cup uye Charity Shield muna 2000, uye akasvika 2002 FA Cup Final. Akabatsirawo mukukunda kweChelsea mu1999-2000 UEFA Champions League. Yakanga ichizoguma nemoyo wakaputsika kuna Babayaro sezvo akatumirwa kunze munguva yekuwedzera vachipesana neBarcelona, sezvavakapfugama kunze kwemakwikwi muchikamu chekupedzisira. Akatarisana nemakwikwi kubva kuna Graeme Le Saux mukati memakore ake manomwe, asi akakwanisa kutamba mitambo inodarika mazana maviri yechikwata cheLondon. Mhemberero dzake dzomutambo dzomumashure dzakacherechedzwa uye dzakadikanwa navateveri vekirabhu. 