Radcliffe, Northumberland born left half Andy Smailes initially played as an inside forward for Blyth Spartans, whom he joined after the First World War in 1918, from where Smailes joined First Division Newcastle United for £300 in October 1919. He made his Football League debut in December the same year at Sheffield United and scored 10 times in his debut season followed by 18 goals in the 1920-21 campaign as Newcastle finished 5th in the League Championship, before converting to the half back line.
After 30 goals in 77 appearances for The Toon, Smailes joined Second Division Sheffield Wednesday for £1,500 in October 1922, scoring 15 goals in 40 appearances for The Owls before Alex Raisbeck signed Smailes for Bristol City in an exchange deal with Billy Walker in October 1923. Despite their relegation during his first season Smailes was an ever present in 1924-25 and then helped them to promotion when they won the 1926-27 Third Division (South) Championship,
After 15 goals in 169 appearances for The Robins Smailes moved on to Rotherham United in August 1929, scoring once in 31 appearances before hanging up his boots in 1932. After retiring Smailes spent 18 years as trainer at Rotherham United before succeeding Reg Freeman as manager in August 1952, with the club spending the duration of his tenure in the Second Division. Smailes resigned as manager of Rotherham in October 1958. Smailes also managed Scarborough for two years.
Smailes had two younger brothers who played professional football; Matt played for Blackburn, West Ham and Coventry City, and Jimmy played for amongst others Huddersfield Town, Tottenham Hotspur, Blackpool and Grimsby Town (all while they were in the top flight).