Born in Wimbledon, London, he began his career in Northern Ireland with Derry City and Glentoran, before returning to England to play for Burnley, Reading, Bolton Wanderers, Portsmouth, Sheffield United and Aldershot Town.

After Stan Ternent's arrival at Turf Moor in summer 1998, he became a fixture in the right-wing slot, linking up especially well with full-back Dean West.

Little made his Premiership debut for the Trotters against Wolverhampton Wanderers and set up the equalising goal for Kevin Davies but his time with Sam Allardyce's team was brief.

Little's talents were widely regarded as one of the main reasons behind Reading's record breaking 106-point Championship lifting 2005–06 season, with Little scoring five goals and setting up fourteen, more than any other player in the league.

Following Reading's narrow relegation in 2008, and Little's injuries leading to a lack of first team action during the 2007–08 season, he opted to sign for Portsmouth on a one-year contract, on 20 June 2008.

[4] Reading, however, failed to gain promotion so Little returned to Portsmouth, where he was released at the end of the 2008–09 season playing in just one game for the FA Cup holders.

[6] Despite this, he struggled to make an impact and made only 16 league appearances for the Blades, many as a late substitute and was released by the South Yorkshire club when his contract expired.

[8] Little eventually made his debut for Wrexham on 10 September 2011, in a 3–1 loss at Barrow; he appeared sporadically over the first half of the 2011–12 season, usually coming on as a late substitute.

On Boxing day 2012 and after three months out with his knee injury Little returned to action in a 4–1 home league win against AFC Telford United.

On 24 March 2013 Little picked up only his third honour in his 18-year career, as Wrexham won the FA Trophy by beating Conference promotion rivals Grimsby Town on penalties.

[11] His first goal in a royals shirt came in an FA Trophy First Qualifier Round, a competition Little had won last season with Wrexham, he scored in a 3–0 win over Leiston.

Upon the conclusion of the 2013–14 season, Little left Wealdstone for personal reasons signing a contract at Isthmian League North side Heybridge Swifts in May 2014.

[12] Little stayed at the club for just over a month before he decided to leave after the departure of manager Jody Brown to Grays Athletic; Little did not make any appearances for the Swifts.

In July 2014 Little opted to follow manager Jody Brown to Essex-based Isthmian League Premier Division side Grays Athletic.