Hollands made his Bournemouth debut on 8 August 2006, where he made his first start and played the whole game, in a 0–0 draw against Yeovil Town. After suffering from a groin injury, he scored his first Bournemouth goal of the season on 3 November 2006, in a 4–2 win over Swansea City. He scored again on 11 November 2006, in the first round of FA Cup, in a 4–0 win over Boston United. From that moment on, Hollands had a run in of first team football under management of Kevin Bond as the 2006–07 season progressed. In his first season, Hollands went on to make thirty–eight appearances and scoring two times in all competitions. For his performance, he was the club's goal of the season, as well as, PFA supporters' player of the month.