Before Ashley arrived at the Port Adelaide Football Club he had already made an impression in Sydney where he had been playing. He represented New South Wales at the inaugural state carnival. A follower, Ashley would later become a regular for South Australia at interstate level. He was a best and fairest winner at Port Adelaide in 1914 and also won that year's Magarey Medal. The war interrupted the SAFL but when it returned in 1919 so did Ashley and he won another best and fairest award before retiring at the end of the season.