1990–91 Kent Football League

The 1990–91 Kent Football League season (known as the Winstonlead Kent League for sponsorship reasons) was the twenty-fifth in the history of the Kent Football League, a football competition featuring teams based in and around the county of Kent in England.

The League structure comprised two divisions: Division One and Division Two with the latter known as the Reserves Section (reserves teams were not permitted in Division One). Additionally there were two league cup competitions: the Challenge Cup for the Division One clubs and another for the teams in Division Two.

Division One
The league featured twenty-one clubs, twenty of which competed in the previous season together with one additional club:
 * Sheppey United, relegated from the Southern League

The league was won by Sittingbourne, the only Kent League winning club (as of 2024) to be unbeaten over the season; it was their third Kent League title and they were subsequently promoted to the Southern Football League.

At the end of the season both bottom clubs, Metropolitan Police (Hayes) and Sheppey United, were re-elected to continue their membership of the division.

Challenge Cup
The 1990–91 Kent Football League Challenge Cup was won by Faversham Town for the second occasion, their first being twenty seasons previously.

The competition, contested by all twenty-one clubs in Division One, comprised five single match tie rounds (with the first round featuring five ties) culminating in the final which was played on a neutral ground (at Whitstable Town F.C. this season).

Second Round

 * Ramsgate 2 – 1 Deal Town
 * Darenth Heathside 3 – 2 Sittingbourne
 * Alma Swanley 4 – 2 Whitstable Town
 * Slade Green 2 – 1 Tonbridge
 * Tunbridge Wells 6 – 0 Beckenham Town
 * Metropolitan Police (Hayes) 1 – 3 Chatham Town
 * Faversham Town 6– 0 Thames Polytechnic
 * Herne Bay 0 – 1 Danson

First Round
Sources:
 * Ramsgate 4 – 0 Crockenhill
 * Darenth Heathside 3 – 0 Cray Wanderers
 * Alma Swanley 1 – 0 Kent Police
 * Replay: Alma Swanley 3 – 1 Kent Police
 * Herne Bay 3 – 0 Sheppey United
 * Greenwich Borough 1 – 4 Danson
 * Byes for the other eleven clubs
 * Final:
 * Semi-finals:
 * Quarter-finals: ;
 * Second Round: ;
 * First Round: ;

Reserves Section
The letter "R" following team names indicates a club's reserves team.

Division Two featured reserves teams (which were not permitted in Division One) from clubs from Kent and the adjacent area whose first team played in Division One and other higher ranked leagues. There was a League Cup competition for the teams in the section.

Division Two
The league featured sixteen reserves teams, fifteen of which had competed in the division the previous season together with one additional club:
 * Deal Town R, returning after a one season absence.

The division was won by Canterbury City R.

Division Two Cup
The 1990–91 Kent Football League Division Two Cup was won by Fisher Athletic R, the only Division 2 Cup win for the club that had won four divisional titles in the 1980s.

The competition, contested by all sixteen clubs in the division, comprised four single match tie rounds culminating in the final

First Round
Sources:
 * Sheppey United R 2 – 8 Whitstable Town R
 * Deal Town R 1 – 2 Hastings Town R
 * Ramsgate R 2 – 1 Cray Wanderers R
 * Dover Athletic R 1 – 3 Beckenham Town R
 * Sittingbourne R 1 – 0 (Thames Polytechnic R
 * Herne Bay R v Margate R
 * Faversham Town R 0 – 4 Fisher Athletic R
 * Ashford Town R 0 – 2 Canterbury City R
 * Final:
 * Semi-finals: ;
 * Quarter-finals: ; ; ;
 * First Round: ; ;