Buuxi weedha soo socota: Intii uu u ciyaarayay Toronto Red Wings, Bolland waxaa loo doortay wareegga koowaad, siddeedaad guud ahaan, ee 2002 Ontario Hockey League Xulashada mudnaanta leh ee London Knights. Wuxuu OHL ugu soo biiray Knights xilli ciyaareedkii 2002-03, halkaas oo uu ku duubay 17 dhibcood 63 ciyaarood. Intii lagu guda jiray xilli ciyaareedkiisii labaad ee OHL, Bolland wuxuu kordhiyay waxqabadkiisa weerarka ee Knights isagoo leh 37 gool iyo 30 caawin oo ah 67 dhibcood. Waxaa sidoo kale loo magacaabay Ciyaaryahanka ugu Horumarka badan naadiga. Bolland wuxuu matalayay Shirweynihii Galbeedka ee 2004 OHL All-Star Game waxaana sidoo kale loo doortay inuu kaqeyb galo 2004 CHL Top Prospects Game. Waxay ku sii jeedeen
2004 NHL Entry Draft, Bolland wuxuu ahaa kaalinta siddeedaad ee ciyaaryahanka kubbadda cagta ee Waqooyiga Ameerika ee NHL's Central Scouting Bureau. Bolland waxaa doortay Chicago Blackhawks wareega labaad, 32aad guud ahaan, ee 2004 NHL Entry Draft.