Gillingham debut, where he came on as a second-half substitute and played 38 minutes, in a 1–1 draw against Bristol City. He scored his first goal for Gillingham in a 3–2 win over Milton Keynes Dons on 5 October. From that moment on, Hollands quickly became a first team regular at Gillingham in the midfield position for the club and since his debut, he started every match until he suffered an injury during a 2–2 draw against Peterborough United on 14 December 2013, resulting him being substituted. Following this, he never played again and returned to his parent club in early–January. Portsmouth On 27 March 2014, Hollands joined Portsmouth on loan for the remainder of the campaign. Hollands made his Portsmouth debut two days later on 29 March 2014, where he started the whole game, in a 2–1 win over Newport County. Hollands scored his first goal on 12 April 2014, in a 4–1 win over Dagenham & Redbridge; followed up by scoring in the next game on 19 April 2014, in a 3–2 win over Bristol Rovers. After adding his third goal, in a 4–4 draw against Bury on 26 April 2014, He scored a hat-trick on the last day of the season against Plymouth Argyle, and contributed with six goals in seven appearances for "Pompey" during his loan spell. 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 an unused substitute on two occasions 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. In the 2015–16 season, Hollands was often