Seasons 1982/83 to 1984/85. During this time Sid Jest and later Bryan Clifton had a go at management. Lester Smith took over for 1985/86 and he immediately caused an improvement in the clubs fortunes. Ramsgate were Eighth that season and Fourth in 1986/87. In 1987/88 they won the Kent Senior Trophy, beating Faversham Town 1-0, at Canterbury. Vic Medus became player manager for the 1988/89 season, when Smith stepped down, and they again lifted the Kent Senior Trophy. This was the Rams only success under Medus and he made way for former Ramsgate and Whitstable forward, Paul Rimmer to take over the managerial reins. Rimmer's term in charge was short lived as he was forced to resign due to pressure of work from his transport business. Former Thanet United, Folkestone Town, Herne Bay and Dover Athletic striker, Lennie Lee was appointed manager and he led them to cup triumphs in the Kent League Division One Challenge Cup in 1992/93, 1993/94 and 1994/95. Following each of those cup successes the Rams were invited to play for the Charity Shield against the League Champions and after a disappointing loss in the first year they lifted the shield for the following two seasons.

The appointment of Jim Ward as manager for 1996/97 saw Ramsgate surge to the top of the league where they remained for most of the season, only to be pipped at the post on the very last day of the campaign.