Ku qor sii wadida cutubkan - Roy wuxuu hogaamiyay Kitchener Rangers ee Ontario Hockey League (OHL) oo leh 87 dhibcood inta lagu gudajiray xilli ciyaareedkii 1999-2000 wuxuuna ku guuleystay koobka OHL Rookie of the Year. Xilli ciyaareedkii xigay, wuxuu dhaliyay 42 gool iyo 81 dhibcood ka dib waxaa loo qoray 32aad guud ahaan Buffalo Sabres ee 2001 NHL Entry Draft
dhamaadka xili ciyaareedka. Xilli ciyaareedkii xigay, 2001-02 Roy wuxuu dhigay xirfadiisa OHL ee 43 gool iyo 89 dhibcood wuxuuna sii waday inuu noqdo goolhayaha ugu sareeya Rangers.