Terry ya fara kafa kansa a cikin tawagar farko ta Chelsea daga kakar 2000-01, yana yin wasanni 23 kuma an zabe shi dan wasan kungiyar. Ya ci gaba da ci gaba a lokacin 2001-02, ya zama na yau da kullum a cikin tsaro tare da kyaftin din kulob din da kuma Faransa na kasa da kasa Marcel Desailly. A ranar 5 ga Disamba, 2001, ya jagoranci Chelsea a karo na farko, a wasan League da Charlton Athletic. Chelsea ta kai wasan karshe na gasar cin kofin FA, bayan cin nasara da abokan hamayyarta na London West Ham United da Tottenham Hotspur a zagaye na hudu da shida, da kuma Fulham a zagaye na karshe <unk> inda Terry ya zira kwallaye guda daya a nasarar 1 <unk> 0.
5 ga Disamba 2001