Ashley began racing in 1966 after taking a course at the Jim Russell Racing School. Fast but erratic, he quickly earned the nickname by which the paddock would know him. He reached Formula 5000 by 1972 and was a front-runner in that category in 1973, contesting non-championship Formula One events at the same period — including the International Trophy and the Race of Champions — in a Formula 5000 Lola for various entrants.
Ashley made his Formula One World Championship debut at the 1974 German Grand Prix with the Token team, driving a Token RJ02-Cosworth. He went on to enter for Williams in 1975, driving the FW03, BRM in 1976 with the P201B, and Hesketh in 1977 with the 308E. Across those four seasons he made eleven World Championship entries and converted four into race starts, scoring no points.
Two accidents defined his Formula One years. During practice for the 1975 German Grand Prix at the Nürburgring he crashed at the Pflanzgarten section and broke both ankles. He recovered and returned to the grid. In practice for the 1977 Canadian Grand Prix at Mosport Park, his Hesketh struck a bump, flipped, vaulted the barrier, and crashed into a television tower. Ashley never raced in Formula One again. His last championship entry — the 1977 Canadian Grand Prix — was listed as a DNS.
In the mid-1980s Ashley moved to the United States to race in CART. His debut came at the 1985 Miami Grand Prix with Tom Hess Racing, where he finished 18th and was classified 48th in the season standings with no points.
In 1986 with Dick Simon Racing he made three CART starts: 15th at Toronto, 9th at Mid-Ohio, and 23rd at Road America. His best result that year was the ninth at Mid-Ohio, which placed him 28th in the championship on 4 points. He was entered for the 1986 Indianapolis 500 but the car did not appear on track. He also made a single Indy Lights start at Pocono Raceway, finishing sixth.
In 1987, again with Dick Simon Racing, Ashley made one CART start at Miami, where he was eliminated by drivetrain trouble and was classified 20th.
Between his American seasons, Ashley built a career as an executive jet pilot in the United States. In 1993 he returned to circuit racing in Britain, driving a Vauxhall Cavalier in the British Touring Car Championship — first for Tamchester Team Maxted and later for Colin Davids Racing — finishing 23rd in the championship. He subsequently raced motorcycle sidecar combinations and competed in the TVR Tuscan Challenge one-make series.
In November 2009, Ashley entered single-seater competition for the first time in more than forty years, driving an Elden MK8 in the Walter Hayes Trophy Formula Ford race at Silverstone.
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