Ashley graduated through the Wolverhampton Wanderers youth system to win a contract with Cheltenham Town in May 2004. He spent the next five years at the club, playing in the 2006 League Two play-off final victory. He was loaned out to Aldershot Town in November 2005 and to Colchester United in March 2009, before he joined Colchester permanently in May 2009. He spent three years with the club, before he moved on to Port Vale in July 2012. He helped the "Valiants" to secure promotion out of League Two in 2012–13, before he re-joined Cheltenham Town in July 2013. He signed with Shrewsbury Town in May 2014, and played a role as the club won promotion out of League Two in 2014–15. He joined Worcester City in August 2015, and then Stourbridge in January 2016.

Tooth had this to say about his latest signing, "Ash is another lad that iv been trying to sign for a while. He is exactly what we need in and around the club as he is a fantastic player and his experience will be invaluable. I'm delighted to finally get him to sign and I'm sure he will quickly become a fans favourite."

We also spoke Ashley who said the following, "I'm very happy to be joining the club, at what seems to be a good time where things are moving forward both on and off the pitch. Hopefully I can bring my experience and quality to the club and have a successful time personally but most of all help the team achieve something special. If along the way I can help some of the other boys too then I'd be more than happy to do so as we'll need to stick together and be strong as a team to achieve any goals set out by the gaffa for the season."

From all at the club Welcome to the Royals Ashley.