From this season onwards the grounds where Premier Division matches were played were required to have floodlights.
At the end of the season Crockenhill resigned and joined the Kent County League.
The 1998–99 Kent Football League Challenge Cup was won by Deal Town.
[3] The 1998–99 Kent Football League Division One Cup was won by Dover Athletic R.[8] The competition for the 19 teams from the Division One comprised five rounds: the first three were a single match knock-out followed by the semis-finals on an aggregate basis (home and away matches) and a single match final.
it was agreed to move it to the home ground of one of the two competing clubs - Dover Athletic won the coin toss.