Bolland played for Orient during their only season in the English top flight, and scored 19 goals in 64 league games before joining Norwich City in 1964 for £31,500, where he scored 29 goals in 105 league matches. After a brief spell with Charlton Athletic, Bolland signed for Millwall for £10,000 in October 1968. Bolland proved to be a fast, skillful striker who could also drop into midfield to great effect. It was from this position that Bolland scored a spectacular goal against Bristol City on 16 October 1971 which won the Match Of The Day "Goal of the Month" award. In the 1972-73 season, Bolland scored 9 goals in seven consecutive league games. He remained with Millwall for seven years, scoring 62 goals in 244 games, and is an inductee of the club's Hall of Fame. He finished his career as player-manager of Boston United.