 Nyorai kuenderera mberi kweiyi ndima - Akawanawo kutaridzika kwechikwata chekutanga chakaganhurirwa pasi pemutambi-maneja Ruud Gullit mumwaka wa1996-97. Zvisinei akaita mitambo mitanhatu muFA Cup uye aive mumwe wevatatu vepakati-kumashure vamwe vari Frank Leboeuf naSteve Clarke kutanga mumakwikwi ekupedzisira a1997 pavakakunda Middlesbrough 20 kusimudza mukombe. Mumwaka unotevera, Sinclair akatamba mu1997 FA Charity Shield sezvo Chelsea yakarasikirwa neManchester United mushure mekupotsa chirango chekutanga. Musi wa9 Nyamavhuvhu, akarova misoro yemapepanhau mushure mekupemberera chinangwa chakanangana neCoventry City nekuburitsa bhurugwa rake; akazotsanangura kuti akazviita mukukudza mwanasikana wake achangoberekwa. Akapfuurira kunyorera Chelsea muLigi Cup yekupedzisira, zvakare pamusoro peMiddlesbrough, mukukunda 2 ku0. Mukana wake wekutanga wechikwata wakanga uchitanga kuve wakaganhurirwa, sezvo maneja mutsva Gianluca Vialli akavaka timu nyowani, iyo yainyanya kuve nyeredzi dzemakondinendi kusanganisira vepakati-kumashure Frank Leboeuf naMarcel Desailly, apo John Terry aiuya kuburikidza nechikwata chevechidiki. Akarasikirwa ne UEFA Cup Winners Cup yekupedzisira kukunda pamusoro peVfB Stuttgart nekuda kwekukuvara kwemhuru, kunyangwe akaita kuoneka kushanu mumakwikwi. Nemhaka yekukuvara uye kukwikwidzana kwenzvimbo dzeLigi Cup yekupedzisira neMiddlesbrough chaizvoizvo yakaratidza kuva kuonekwa kwake kwekupedzisira kwechikwata. 