Kammala wannan jumla: Roy an rubuta shi a zagaye na uku, na 51 a cikin duka, a cikin
1984 NHL Entry Draft ta Montreal Canadiens, ƙungiyar da bai so ba, kasancewar mai son abokin hamayyar Quebec Nordiques. Kakarsa Anna Peacock babbar magoya bayan Canadiens ce, amma ta mutu kafin ta ga an tattara jikanta. Roy ya ci gaba da bugawa Granby Bisons na Quebec Major Junior Hockey League (QMJHL) kafin Canadiens ya kira shi. Duk da tunanin cewa ba zai buga wa kungiyar wasa ba, a ranar 23 ga Fabrairun 1985, ya fara buga wasan NHL lokacin da ya maye gurbin mai tsaron gida na Canadiens, Doug Soetaert, a cikin wasan na uku. Roy ya buga minti 20 kuma ya sami nasararsa ta farko a NHL ba tare da barin wata manufa ba. Bayan wasan, an sake sanya shi zuwa Sherbrooke Canadiens na AHL. Duk da farawa a matsayin madadin, Roy ya maye gurbin Greg Moffett bayan ya sami matsalolin kayan aiki yayin wasa. Ya sami nasara, ya zama mai tsaron gida na farko don wasan kwaikwayo kuma ya jagoranci tawagar zuwa gasar cin kofin Calder tare da nasara goma a wasanni 13.