Oliver was born in Glasgow and joined Heart of Midlothian's youth academy in Edinburgh. Oliver's professional debut for Hearts was in a Scottish League Cup match against Raith Rovers on 27 August 2013, coming on as a substitute in the 55th minute, replacing midfielder Scott Robinson. Four days later Oliver made his league debut for the club, coming on as substitute for Callum Tapping in the 61st minute in a 2–0 defeat to Inverness Caledonian Thistle. Under the management of Gary Locke, Oliver was one of the youngsters to get an opportunity in the first team, as a result of Hearts entering administration, as well as having an injury crisis at that particular time. Oliver ended his first season at the club with 8 league appearances, as Hearts were relegated to the Scottish Championship. His season, however, was overshadowed when he injured his ankle during a match against Inverness Caley Thistle and was sidelined for three weeks. Oliver signed a new one-year contract extension after Hearts ended their period of administration. On 23 August 2014 Oliver scored his first goal for Hearts in a 4–0 win over Raith Rovers, scoring in the 90th minute. On 1 September 2014 Oliver joined Scottish League One club Stenhousemuir on loan until 5 January 2015. Ironically, Oliver then played against the Ochilview Park club later that season during March 2015, after his loan spell had ended, scoring a goal as Hearts won 2–1. During his loan spell at Stenhousemuir, Oliver had scored two goals and set-up another goal in a 4–0 win over Stirling Albion on 19 October 2014. On 19 December 2014 Oliver's loan spell at Ochilview ended early, as he was recalled by Hearts after appearing in 11 league matches and scoring two goals. After one season in Dumfries, Oliver signed for his uncle Jim Duffy's club Greenock Morton. After his two-year deal ended, Oliver signed a one-year contract extension with the Greenock club. In November 2018, Oliver sustained a broken collarbone in a challenge with Peterhead's ex-Ton midfielder Jamie Stevenson, that kept him out of first-team action for two months. On 10 June 2019, Oliver signed a two-year contract with Dumfries club Queen of the South, where he returns for a second spell.
International career
During October 2013, Oliver was called up by Ricky Sbragia for the Scotland under-19 squad. Oliver made his Scotland U19 debut in a 1–1 draw against Germany under-19's and scored his first goal in a 4–2 win over Switzerland under-19's.
Career statistics
Personal life
Oliver was born in Glasgow and attended Cleveden Secondary School. Oliver is the nephew of the current Greenock Morton manager Jim Duffy.
