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Oliver signed for League Two club Northampton Town on 3 July 2019 on a one-year contract.

On 21 May 2017, Oliver started as York beat Macclesfield Town 3–2 at Wembley Stadium in the 2017 FA Trophy Final, scoring in the 22nd minute with a three-yard shot from Sean Newton's low cross. He finished 2016–17 with 10 goals from 23 appearances for York as the club was relegated to the National League North after finishing in 21st place in the National League. He was transfer listed at the end of the season at his own request.

Oliver signed for League Two club Morecambe on 30 June 2017 for an undisclosed fee, on a contract of undisclosed length. He scored his first goal for Morecambe in a 4–3 EFL Cup defeat away to Barnsley on 8 August 2017. He was released by Morecambe at the end of the 2018–19 season.

On 2 August 2016, Oliver joined League Two club Notts County on loan until 7 January 2017. He debuted four days later as a 56th-minute substitute for Jon Stead in a 2–0 defeat away to Yeovil Town. He scored his first goal for the club in a 2–1 loss against Morecambe on 11 October 2016.

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.

He attracted interest from Football League clubs and signed for League One club Crewe Alexandra on 10 June 2013 on a two-year contract for an undisclosed fee. He made his debut as an 89th-minute substitute in a 3–3 draw with Rotherham United on 3 August 2013. Oliver scored his first Crewe goal after sliding in from a Brad Inman cross in the 15th minute of a 2–2 draw at home to Peterborough United on 7 September 2013.

Oliver was born in Sheffield, South Yorkshire. He began his career with Sheffield Wednesday's youth system, and signed a professional contract in 2010. He was released by the club in May 2012, before joining Conference Premier club Lincoln City on 4 August 2012 on a one-year contract. He scored 13 goals for Lincoln in the 2012–13 season, 11 of which came in the league.

Vadaine Aston James Oliver (born 21 October 1991) is an English professional footballer who plays as a striker for League Two club Northampton Town. He has played in the English Football League for Crewe Alexandra, Mansfield Town, York City, Notts County and Morecambe.