[1] Born in Lincolnshire, England, Chatterton's motorcycle road racing career spanned thirty years, beginning in 1961 at the age of 16.

[citation needed] His first race was at Cadwell Park in Lincolnshire on a 1949 250 cc (15 cu in) Velocette, early promise that year didn't initially translate to good results until Mallory Park at the end of the season where Chatterton, riding an NSU Sportmax, finished third in the Junior race collecting 'Rider of the Meeting' in the process.

[2] In 1974 Chatterton scored an impressive 500cc class victory over multi-time world champion Giacomo Agostini at Cadwell Park.

[4] He was also a two-time winner of the North West 200 road race in Northern Ireland, winning the 250cc event in 1971 and 1975 on a Yamaha.

Chatterton was a regular Isle of Man TT competitor from 1968 until 1991, his best result was a second-place finish in the 1975 Lightweight 250cc race on a Chat Yamaha.