On 22 May 2014, Hollands joined Portsmouth in a permanent basis, signing a two-year deal. Upon joining the club, he was given a number 29 shirt, a shirt he wore whilst on loan. He made his second Portsmouth debut in the opening game of the season, in a 1–1 draw against Newport County. But following Ben Chorley's injury, he captained the side for the first time on 16 September 2014, in a 3–0 win over Dagenham & Redbridge. Hollands scored his first Portsmouth goal since joining them on a permanent basis, in a 3–0 win over Carlisle United on 1 November 2014, followed up by scoring in a 2–2 draw against Aldershot Town in the first round of FA Cup. Hollands then captained the side once again on 17 March 2015, in a 2–2 draw against Cheltenham Town. Despite appearing as unused substitute bench on two occasion and being once left out of the squad in late–December, Hollands finished the 2014–15 season, making forty–eight appearances and scoring two times in all competitions.