Born in Sittingbourne, Andy Drury began his career with his hometown club in 2001 before moving on to Gravesend & Northfleet (now Ebbsfleet United) and Lewes where he won the Conference South.

After signing for Conference Premier side Stevenage Borough in 2008, he went on to win the FA Trophy in 2009 before promotion to the Football League in 2010.

Moved back into the Conference Premier with Luton Town for the start of the 2010/11 season before joining Championship side Ipswich Town in January 2011.

Had a spell on loan at Crawley Town in 2011 before joining permanently upon his departure from Ipswich in 2013. Rejoined Luton (then in League 2) in 2014.

Returned to non-league football in 2015 for a 2-year spell at Eastleigh followed by 2 years at Ebbsfleet United where he won promotion to the National League and 2 years at Havant & Waterlooville.

Returned to his hometown club Sittingbourne in 2020 before joining Cray Wanderers as player-coach under Danny Kedwell.

After departing Cray, he joined Folkestone Invicta for the first time as a player in January 2022 for a 2-month spell before taking up a managerial post at Whitstable Town.

Joined Margate as manager in the summer of 2022 before departing in December, joining Chatham Town as a player where he won the Isthmian South East Division title.

Returned to Invicta as a player-coach under joint managers Micheal Everitt and Roland Edge in the summer of 2023 before taking over as manager in December.