Early days at Carlisle
Ashman had an undistinguished amateur playing career with Sheffield United F.C. and Nottingham Forest F.C. during the ad hoc competitions of World War II. In 1951, he signed for Carlisle United F.C. for whom he made 207 appearances, scoring 98 goals. In 1958, suffering from cartilage damage, he retired from playing to manage the poultry farm of Mr Monkhouse, one of the club's directors. As a recreation, he managed amateur team Penrith F.C. and when Third Division Carlisle found themselves in need of a manager in February 1963, Mr Monkhouse offered Ashman the job.
Starting off in management
Ashman was too late to prevent that season's relegation but the following season saw a bounce back, and the season after that, the Third Division championship. Leading Division Two for much of the 1965/1966 season, the club was disappointed to miss out on promotion by finishing third.
Cup glory with the Baggies
Ashman's exploits had not gone unnoticed and, in 1967, he joined West Bromwich Albion F.C., leading them in a series of exciting cup runs, crowned by victory in the 1968 FA Cup. His new club was, however, impatient for further trophies and he was dismissed in 1971, hearing of the news from a waiter while on holiday in Greece. Somewhat ironically, he went on to manage Olympiakos before returning to Carlisle in August 1972, leading the club to the First Division and a brief spell at the top of the entire English league.
The heights were short-lived and Ashman left the club to manage Workington F.C. and Walsall F.C. before settling for junior coaching and scouting roles at Derby County, Hereford United and Swallows of Walsall.