In the 2007–08 season, Hollands said his aim this season was to "improve as a player" in order to get first team football. However, he missed out the start of the season, due to a hamstring injury. After returning to the first team in early–September, he scored his first goal of the season, in a 4–1 loss against Swindon Town on 22 September 2007. It wasn't until on 20 November 2007 when he scored again, but was sent–off for a second bookable offence, in a 3–2 win over Barrow in the second round replay of the FA Cup. However, during the match against Barrow, he suffered a hernia injury in the process. After an eventual recovery from the injury and served two match suspension, he returned to the first team and then scored again on 26 January 2008, in a 3–1 win over Port Vale. A week later, on 2 February 2008 against Nottingham Forest, Hollands captained the side for the first time in his career, which saw them win 2–0. Despite being sidelined twice, due to "dead leg" injury and suspension, he scored again on 15 March 2008, in a 2–0 win over Yeovil Town. Hollands also scored his fifth goal on 19 April 2008, in a 3–1 win over Walsall. However, despite good performances and effort as the season progressed, the club were relegated to League Two, due to the club entered administration along the way. At the end of 2007–08 season, Hollands went on to make forty–three appearances and scoring five times in all competitions. For his performance, Hollands was awarded the Daily Echo/Micky Cave's Player of the Year.