1998–99 Kent Football League

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.

Premier Division
The league featured 19 clubs which had competed in the previous season, no additional clubs joined the league this season.

The league was won by Ramsgate for the second season in succession.

At the end of the season Crockenhill resigned and joined the Kent County League.

Challenge Cup
The 1998–99 Kent Football League Challenge Cup was won by Deal Town.

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. this season).

Quarter-finals, Semi-finals and Final
Sources:
 * Quarter-finals: ;
 * Semi-finals: ;
 * Final:

Second Round

 * Chatham Town 2 – 0 Slade Green
 * Beckenham Town 2 – 3 Deal Town
 * Cray Wanderers 1 – 0 Lordswood
 * Whitstable Town 0 – 2 Ramsgate
 * Herne Bay 1 – 0 Tunbridge Wells
 * Canterbury City 1 – 3 VCD Athletic
 * Erith Town 0 – 2 Crockenhill
 * Faversham Town 2 – 2 Hythe United (match abandoned after 84 minutes owing to floodlight failure)
 * REPLAY: Hythe United 3 – 1 Faversham Town

First Round
Sources:
 * Chatham Town 4 – 1 Greenwich Borough
 * Sheppey United 0 – 3 Deal Town
 * Thamesmead Town 0 – 2 Crockenhill
 * Byes for the other 13 teams
 * Second Round: ;
 * First Round:

Reserves Section
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.

Division One
The division featured teams from 19 clubs, 16 of which were from the previous season together with three additional teams
 * Swanley Furness who had dropped from the top division and replaced their reserves team.
 * Canterbury City R
 * Cray Wanderers R

The division was won by Deal Town R.

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.

Division One Cup
The 1998–99 Kent Football League Division One Cup was won by Dover Athletic R.

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.

Quarter-finals, Semi-finals and Final
Sources:
 * Quarter-finals: ; ; ;
 * Semi-finals: ;
 * Final:

Second Round

 * Swanley Furness 4 – 3 Chatham Town R
 * Whitstable Town R 3 – 3 Lordswood R (score at 90 mintues: 3–3)
 * REPLAY: Lordswood R 0 – 2 Whitstable Town R
 * Ramsgate R 1 – 1 (aet) Sittingbourne R (score at 90 mintues: 1–1)
 * REPLAY: Sittingbourne R 1 – 0 Ramsgate R
 * Cray Wanderers R 1 – 1 (aet) Dover Athletic R (score at 90 mintues: 0–0)
 * REPLAY: Dover Athletic R 2 – 1 Cray Wanderers R
 * Canterbury City R 2 – 5 Hythe United R
 * Crockenhill R 0 – 1 Deal Town R
 * Hastings Town R 2 – 5 Folkestone Invicta R
 * Thamesmead Town R 1 – 2 Dartford R

First Round
Sources:
 * Herne Bay R 0 – 1 Cray Wanderers R
 * Margate R 1 – 2 Hythe United R
 * Dartford R 3 – 2 Beckenham Town R
 * Byes for the other 13 teams
 * Second Round: ; ; ; ; ;
 * First Round: ; ;