Kammala jumla mai zuwa: Yayin wasa don Toronto Red Wings, an zaɓi Bolland a zagaye na farko, na takwas gaba ɗaya, na Zaɓin fifiko na 2002 na Ontario Hockey League ta London Knights. Ya fara buga wasan OHL tare da Knights a lokacin kakar 2002-03, inda ya zira kwallaye 17 a wasanni 63. A lokacin da yake shekara ta biyu a OHL, Bolland ya kara yawan gudummawar da ya bayar ga Knights tare da kwallaye 37 da tallafi 30 don maki 67. An kuma sanya shi a matsayin mafi kyawun dan wasan kungiyar. Bolland ya wakilci taron Yammacin Turai a wasan 2004 OHL All-Star Game kuma an zaba shi don shiga cikin wasan 2004 CHL Top Prospects Game. Yana zuwa cikin
2004 NHL Entry Draft, Bolland shi ne na takwas da aka zaba a Arewacin Amirka ta hanyar NHL ta Central Scouting Bureau. Bolland ya zaba ta Chicago Blackhawks a zagaye na biyu, 32nd gaba ɗaya, na 2004 NHL Entry Draft.