The 1998–99 Kent Football League season (known as the Winstonlead Kent League for sponsorship reasons) was the 33rd in the history of Kent Football League a football competition in England.
The League structure comprised two divisions: a Premier Division together with a Reserves Section league, Division One. The two divisions had been renamed respectively from Division One and Division Two of the previous season. Reserves teams were not permitted in the Premier Division. Additionally there were two league cup competitions: the Challenge Cup for the Premier Division clubs and another for the teams in the Reserves Section.
From this season onwards the grounds where Premier Division matches were played were required to have floodlights.[1]
^Faversham Town were deducted the three points gained from match of 26 September 1998 won 2–1 versus Sheppey United, for fielding an ineligible player.[4]
Challenge Cup
The 1998–99 Kent Football League Challenge Cup was won by Deal Town.[5]
The competition was contested by the 19 teams from the Premier Division over 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 the final match played on a neutral ground (at Folkestone Invicta F.C.[6] this season).
The letter "R" following team names indicates a club's reserves team.
The 1998–99 Reserves Section comprised a single division. The promotion of reserves teams into the Premier Division was not permitted. There was a single League Cup competition for the teams in the section.
At the end of the season Crockenhill R resigned from the league and the remainder of the teams were allocated to two new equally ranked, geographically based divisions, Division One North and Division One South.[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. Although the final was scheduled to be at Herne Bay F.C. it was agreed to move it to the home ground of one of the two competing clubs - Dover Athletic won the coin toss.[9]
^"Football Results And Fixtures Service: Fixtures: Saturday, May 1: Winstonlead Kent League: Premier Division Cup Final". Dover Express. Dover. 29 April 1999. p. 71.