Oliver signed for League Two club York City on 20 May 2015 on a three-year contract. He made his debut when starting York's 3–0 away defeat by Wycombe Wanderers on 8 August 2015, the opening match of 2015–16. His first goal for the club came in the 59th minute of a 3–0 away win over Newport County on 5 September 2015, with a close-range shot after James Berrett's shot was saved. Early in the season, Oliver showed a desire to flick on aerial balls, but once that desire seemingly disappeared he "cut a lethargic figure up front", according to Dave Flett of The Press. He finished the season as York's top scorer with 10 goals from 42 appearances, although he only scored once in his last 19 appearances. Following York's relegation to the National League after finishing 24th in League Two, Oliver was transfer listed by the club.
