Anderton was signed as an apprentice by Portsmouth manager Alan Ball, coming to prominence at 18 when he scored at Anfield in an FA Youth Cup match against Liverpool which ended 2–2.

His performances soon drew the attention of bigger clubs and after an impressive FA Cup run, during which he scored in a semi-final clash with Liverpool, he joined Tottenham Hotspur for £1.75 million in 1992.

[3] After a slow start, Anderton settled at Tottenham, playing as a right winger, forming part of an exciting attacking trio along with Teddy Sheringham and the young Nick Barmby.

He turned down a move to Manchester United in the summer of 1995 following an exciting season spent playing with the likes of Jürgen Klinsmann at Tottenham, a decision that he later regretted.

[6] In the summer of 2001, Anderton was heavily linked with a move to Liverpool, but he remained at Tottenham for the 2001–02 season and started in his second League Cup final, which Spurs lost 2–1 to Blackburn Rovers.

Anderton left Birmingham on a free transfer after one year and reunited with his former Tottenham and England coach Glenn Hoddle at Wolverhampton Wanderers, signing a one-year deal at the start of the 2005–06 season.

[10] On 8 September 2006, Anderton joined League One club AFC Bournemouth on a 'pay-as-you-play' basis, scoring a spectacular 40-yard free kick on his first-team debut against Scunthorpe United.

Anderton spearheaded a survival bid at the end of the season, with the Cherries winning six of the seven last games, but, ultimately, a 1–1 draw with Carlisle on the final day saw Bournemouth relegated to League Two.

[17] In June 1995, Anderton appeared for England at the Umbro Cup mini tournament where he scored the opening goal of a 2–1 win against Japan and a stoppage time equaliser in a 3–3 draw with Sweden.

[24] After missing UEFA Euro 2000 with an Achilles tendon injury,[25] Anderton played in England's 1–1 draw away to France in September 2000 and also featured against Italy the following November.

Renowned as a player of huge potential, Anderton's career was constantly frustrated by injury, earning him the nickname "Sicknote",[19] which was coined by Portsmouth goalkeeper Andy Gosney.