Liam Bailey was with Norwich's Under-10s schoolboy side in 1997/98. The Colchester youngster had already spent some time with QPR before joining Norwich.

He later joined Colchester United wher he endured a severe life-threatening injury. Liam had a minor knock in a match in October 2001, and thought little of it. After six weeks of pain and meeting uncertainty from medics, he began to cough up blood and be sick. He was immediately transferred to Royal Brompton Hospital, in London, where an abscess on his lung was found. The condition became critical and his family Mrs Bailey was warned to prepare for the worst that it could prove fatal. After five days on a life-support machine though, Liam showed signs of recovery and moved to intensive care, amazing doctors with his strength. His recovery was sufficient that he earned himself a place in Colchester's youth team.
Although given a professional contract by Colchester in the summer of 2006, Liam joined Wivenhoe as first-team opportunities were limited so he decided to drop down the divisions in search of regular football. He moved to Braintree during the 2006/7 season.

In July 2008, Liam signed for Stanway Rovers.

In September 2010, he joined Botolphs who play in the Colchester & District Sunday Premier League, and combines it with coaching the youth team at Colchester.

In November 2016, he was promoted to the role of Under-18s manager at Colchester, replacing Norwich-bound David Wright. He was later promoted to Under-21s manager.