Oliver is a central midfielder who went onto the U17 Academy Educational Scholarship scheme as an Under-18 player. Whilst technically sound, his small stature meant he spent much of the 2013/14 season playing with the Manchester United Under-16 side, making only two appearances from the bench for the Under-18 side. In 2014/15 he played more games for the Under-18 side but only as a squad player. He did however score a few vital goals including an outstanding long range effort away to Derby County.
In 2015/16, Oliver had to wait until February 2016 to make his Under-21 debut in a game away at Blackpool. He was released by the club at the end of the season and signed for Rochdale.