Pari gbolohun ti o tẹle: Lakoko ti o nṣere fun Toronto Red Wings, Bolland ni a yan ni iyipo akọkọ, kẹjọ lapapọ, ti 2002 Ontario Hockey League Priority Selection nipasẹ awọn London Knights. O ṣe OHL akọkọ rẹ pẹlu awọn Knights lakoko akoko 2002-03, nibi ti o ti ṣe igbasilẹ awọn aaye 17 ni awọn ere 63. Nigba akoko OHL keji rẹ, Bolland pọ si awọn ọrẹ ikọlu rẹ si awọn Knights pẹlu awọn ibi-afẹde 37 ati awọn iranlọwọ 30 fun awọn aaye 67. Wọ́n tún pè é ní Olùṣeré tí ó dára jùlọ nínú ẹgbẹ́ náà. Bolland soju fun Western Conference ni 2004 OHL All-Star Game ati pe o tun yan lati kopa ninu 2004 CHL Top Prospects Game. Wọ́n ń lọ sí
Ni 2004 NHL Entry Draft, Bolland ni ẹni kẹjọ ti o wa ni ipo North American skater nipasẹ Ile-iṣẹ Central Scouting ti NHL. Bolland ni Chicago Blackhawks yan ni ipele keji, 32nd lapapọ, ti Aṣayan Aṣayan Aṣayan NHL 2004.