Mezue ahịrịokwu na-esonụ: Mgbe ọ na-egwu maka Toronto Red Wings, Bolland họpụtara na agba nke mbụ, nke asatọ n'ozuzu, nke 2002 Ontario Hockey League Priority Selection site na London Knights. O mere OHL mbụ ya na ndị Knights n'oge 2002-03 oge, ebe o dere 17 isi na egwuregwu 63. N'oge afọ nke abụọ ya na OHL, Bolland mụbara onyinye ya na-awakpo ndị Knights na ihe mgbaru ọsọ 37 na enyemaka 30 maka isi ihe 67. A kpọkwara ya onye egwuregwu kachasị mma nke klọb ahụ. Bolland nọchitere anya Western Conference na 2004 OHL All-Star Game ma họrọkwa isonye na 2004 CHL Top Prospects Game. Na-aga n'ime
2004 NHL Entry Draft, Bolland bụ onye nke asatọ North American skater site na NHL's Central Scouting Bureau. Ndị Chicago Blackhawks họpụtara Bolland na agba nke abụọ, nke 32 n'ozuzu, nke 2004 NHL Entry Draft.