Ahead of the 2008–09 season, Hollands was keen on signing a new contract with the club despite their relegation to League Two. As a result, he was linked a move away from Bournemouth, as Colchester United was keen on signing him. In the end, Hollands agreed to stay at the club this season, eventually signing a new contract, keeping him until 2010. However, he missed the start of the season, due to suffering a knee injury. Despite aiming to return to the first team in September, he returned to the first team and scored his first goal of the season, a week later on 2 September 2008, in a 3–0 win over Bristol Rovers in the first round of the Football League Trophy. Following an end to the game against Accrington Stanley on 15 November 2008, which saw them lose 3–0, Hollands was involved in alteration with the club's supporters in the final whistle, prompting to apologise afterwards. By the end of 2008, Hollands went on to score two more goals against Bradford City and Wycombe Wanderers. On 3 January 2009, Hollands scored again, in a 2–1 loss against Darlington, followed up his sending off in the next game, in a 1–0 loss against Rotherham United. After serving a one match suspension, Hollands scored in the next game, on 17 January 2009, in a 1–1 draw against Luton Town. As the 2008–09 season progressed, he went on to score two more goals against Aldershot Town and Exeter City. At the end of the 2008–09 season, he helped the club survive relegation, having started the season with deducted points. He also went on to make forty–eight appearances and scoring seven times in all competitions.