In his most recent managerial role, Andy Hessenthaler was appointed caretaker manager of Leyton Orient in April 2016, and secured the permanent role in June.
As a player, Hessenthaler has over 450 league games to his name - over half for Gillingham, so it was a natural progression when manager Peter Taylor made him player-coach of The Gills, as he played a pivotal role in the club's successful promotion campaign to Division One, during which he was crowned the club's Player of the Year. When Taylor left to take over at Premiership side, Leicester City, he was the logical choice.
He took over as manager on the 29th June 2000; it was in the 2001–02 season, where he led Gillingham to twelfth place and the following season to eleventh place in the First Division - Gillingham's best ever finish in over seventy years in the Football League.
In his first spell, Andy managed Gillingham for 228 games losing only 23% before parting on 23rd November 2004.
Later, he enjoyed success with Dover Athletic, winning two promotions and two league titles before replacing Mark Stimson at Priestfield.
In the 2010/11 campaign, he enjoyed a successful return to the Gills as he was awarded the Manager of the Month for December 2010. The club were also in contention for promotion and just missed out on a place in the play-offs to goal difference.
At the end of the 2011/12 season, Hessenthaler took up the role of Director of Football and in the new campaign Gillingham were promoted to the third tier of English football as the club won the League Two title.
He resigned from the role to get back into management and was promoted to manager at Leyton Orient in 2016 after serving as assistant manager for a season.