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.