During the 1980s, when Jack Ind was Headmaster, the buoyant British economy enabled Dover College to enjoy a period of relative prosperity. However, the 1990s was a period of readjustment for the independent sector as a whole. Martin Wright, Jack Ind’s successor, had the task of leading the College during this difficult period of readjustment.

In 1997, Howard Blackett took over the reins and successfully steered the College before taking up post as Headmaster of The Royal Hospital School in Ipswich. In 2004 Stephen Jones, a Housemaster at Radley, was appointed. During his time, the school saw the creation of a new music department, Tallis, and the renovation of Menzies Hall. He moved to St Edward’s Oxford as Warden in 2011.

Gerry Holden, who had previously been Headmaster of Rendcomb College, started in September 2011, helped to develop the strong family atmosphere for which the College is famed, retiring in December 2014.

In January 2015, Gareth Doodes joined Dover College as Headmaster, and during his time, the school saw a refreshed management structure, a successful ISI inspection, the launch of a new development plan, Project 150. 

From September 2020, Simon Fisher joins the College, bringing a wealth of academic wisdom from his time at Worth School, Sussex.