Ashley joined the Gills in the summer of 2023 from Crawley Town for an undisclosed fee.

The 28-year-old began his career in non-league with Horley Town in the Combined Counties league and his performance altered the attentions of Fleetwood who clinched his signature in the summer of 2016. He made his pro debut the following year during a 2-0 win over AFC Wimbledon at Highbury. 

His first senior goal came while on loan with Carlisle United later that same season, netting against Barnet.

He signed a three-year deal with Crawley in 2019 and in total made 167 appearances for the club, scoring 31 times.

On signing for the Gills he scored three times in his first four outings, scoring against Championship side Southampton in the opening round of the Carabao Cup at Priestfield.