While playing for the Toronto Red Wings, Bolland was selected in the first round, eighth overall, of the 2002 Ontario Hockey League Priority Selection by the London Knights. He made his OHL debut with the Knights during the 2002–03 season, where he recorded 17 points in 63 games. During his sophomore OHL season, Bolland increased his offensive contributions to the Knights with 37 goals and 30 assists for 67 points. He was also named the club's Most Improved Player. Bolland represented the Western Conference at the 2004 OHL All-Star Game and was also chosen to participate in the 2004 CHL Top Prospects Game. Heading into the 2004 NHL Entry Draft, Bolland was the eighth ranked North American skater by the NHL's Central Scouting Bureau. Bolland was selected by the Chicago Blackhawks in the second round, 32nd overall, of the 2004 NHL Entry Draft.