[4][5] Chamberlain started his career with local side Port Vale, making his debut under Dennis Butler as a substitute in a 2–2 home draw with Scunthorpe United on 19 August 1978, aged 16.
[1] Chamberlain then made eleven goalless appearances in 1979–80, whilst his brother was the club's top-scorer in what was Vale's worst season in the Fourth Division.
[1] He scored eight goals during the campaign, most memorably when he stood off the pitch at Field Mill to avoid being caught offside, then returned to tackle a startled Rod Arnold and tap the ball into an empty net.
[7] He was the subject of a £100,000 transfer bid by Potteries derby rivals Stoke City in January 1982, which Vale chairman Don Ratcliffe described as "an insult... attempted robbery; it is a disgrace".
"In September 1985, he moved on to Sheffield Wednesday for a fee of £300,000,[12][13] who went on to finish fifth in the top-flight under Howard Wilkinson in 1985–86, missing out on European football due to the ban imposed on English clubs following the Heysel Stadium disaster.
The "Owls" finished 13th in 1986–87 and 11th in 1987–88, with Chamberlain playing 66 league games before transferring to Alan Ball's Second Division side Portsmouth in August 1988 for a fee of £200,000.
He then helped Jim Smith's side to the FA Cup semi-finals in 1991–92, and featured in the 1–1 draw with Liverpool at Highbury, but not in the replay at Villa Park.
The club finished in third place in 1992–93, missing out on automatic promotion by goal difference, and were beaten by Leicester City at the play-off semi-final stage.
They then finished a disappointing 17th in 1993–94, and Chamberlain moved on to Liam Brady's Brighton & Hove Albion in August 1994, having played 167 games in his six years at Fratton Park.
[11] During the match, teammate Luther Blissett became the first black player to score for England, having bagged two of his three goals before Chamberlain found the net.
[15] He also made a substitute appearance in the 1–0 home defeat to Denmark on 21 September 1983;[16] this crucial result eventually led the Danes to win qualification to Euro 1984 ahead of England.
[11] Stoke City fan and author Simon Lowe wrote that "His slim, athletic build made him seem taller than his modest 5ft 9in height.