Ahead of the 2009–10 season, Hollands was appointed as a new captain. He also agreed on staying after being paid by 12 June 2009 following a 14-day notice from the Football League. However, at the start of the season, Hollands missed out, due to suffering a knee injury. It wasn't until on 5 September 2009 when he returned to the first team, coming on as a late substitute, in a 2–1 win over Torquay United. Between 6 October 2009 and 17 October 2009, Hollands scored three times in three matches against Northampton Town, Chesterfield and Accrington Stanley. By January 2010, Hollands was replaced by Jason Pearce as captain. Manager Eddie Howe went on to explain on removing as a captain, stating that he wanted to concentrate on football and Hollands, himself, agreed on being removed as captain. Despite this, Hollands scored a brace twice later in the season against Rotherham United and Notts County. Despite being sidelined once again, Having helped the club's promotion to the League One for next season, Hollands went on to make forty–two appearances and scoring seven times in all competitions. At the end of the 2009–10 season, Hollands signed a contract extension with the club, keeping him until 2011.