Ashley is a centre forward who might be wrongly thought of as a target man due to his height. He has a good touch and his link-up play improved a lot over the course of the 2013/14 season. With 13 goals and 6 assists in 20 appearances, injury cut his season short.
He made the step up to the Under-21 side during the 2014/15 season, finishing the campaign strongly. Ashley took that confidence into the 2015/16 campaign and showed encouraging signs of development. In January 2016 Ashley joined Barnsley on a one month youth loan but impressed the club sufficiently that it was extended until the remainder of the season. He played a pivotal role in Barnsley's success during the campaign, including helping to fire them to promotion.
At the end of the 2015/16 season Ashley turned down a new contract offer from Manchester United and opted to sign a four year contract with West Ham.