Akaberekerwa muBarking, London, Terry akapinda muEastbury Comprehensive School uye akatambira timu yemuno yeSunday League Senrab, iyo yaisanganisirawo vatambi veChelsea Premier League Sol Campbell, Jermain Defoe, Bobby Zamora, Ledley King naJlloyd Samuel. Semukomana, pakutanga aive chikamu chehurongwa hwevechidiki veWest Ham United, achivabatana semutambi wepakati muna 1991. Akatamira kuChelsea aine makore gumi nemana, achitamba vechidiki vekirabhu uye zvikwata zvekuchengetedza. Yakanga iri nekuda kwekushomeka kwevadziviriri vepakati kuti akaendeswa kunzvimbo yepakati, chinzvimbo chaanotamba nhasi.
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