 Nyorai kuenderera mberi kweiyi ndima - Akaita 756 makwikwi uye makwikwi mumakore 25 ekutamba basa, achiwana zvibodzwa makumi maviri nemanomwe. Mutsigiri, akatanga basa rake kuChelsea, achishandura nyanzvi muna Chivabvu 1990 uye ndokuzoita kutanga kwake muFootball League muna Kubvumbi 1991. Akatamba pachikwereti kuWest Bromwich Albion kubva munaDecember 1991 naKurume 1992. Akazvisimbisa pachake muboka rekutanga kuChelsea munguva ye 1992-93 Premier League mushandirapamwe uye akaenderera mberi achinzi mutambi weClub weGore ra1993. Akatamba parutivi rwunokundwa mufainari yeFA Cup ya1994, asati atora menduru yevakundi mushure mekunge Chelsea yarova Middlesbrough 20 mufainari ya1997. Chelsea yakakundawo League Cup nekurova Middlesbrough 20 mufainari gore rakatevera, uye Sinclair akarova chinangwa chekutanga munguva yekuwedzera. Chelsea yakakundawo UEFA Cup Winners Cup muna 1998, kunyange zvazvo Sinclair akarambidzwa kubva pakupedzisiranemhaka yokukuvara. 