Smokey Featherstone was educated at King Edward VII High School in Johannesburg and toured England with the South African Schools team in 1967.
He made his debut for Transvaal B as a right-handed batsman and an off-break bowler in the 1967/1968 Currie Cup competition. He represented Middlesex between 1968 and 1979, being awarded his county cap in 1971. He scored 8,882 runs in 216 first-class matches with eight centuries and took 137 wickets. He later played for Glamorgan between 1980 and 1981.