The 1985–86 Kent Football League season (known as the Winstonlead Kent League for sponsorship reasons) was the twentieth 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 eighteen clubs, seventeen of which competed in the previous season together with one additional club: Thames Polytechnic, transferred from the London Spartan League
The league was won, for the only time in their history, by Alma Swanley.
At the end of the season both bottom clubs, Slade Green Athletic and Deal Town were re-elected to continue their membership of the division.
League table
Challenge Cup The 1985–86 Kent Football League Challenge Cup was won by Tunbridge Wells, their third win following two occasions during the 1970s.
The competition, contested by all eighteen clubs in Division One, comprised five single match tie rounds (with the first round featuring two ties) culminating in the final which was played on a neutral ground (at Sittingbourne F.C. this season).
Quarter-finals, Semi-finals and Final
<onlyinclude> Second Round Whitstable Town 2 – 1 (aet) Greenwich Borough (score at 90 minutes: 1 –1) Sittingbourne 2 – 1 (aet) Faversham Town Beckenham Town 1 – 5 Darenth Heathside Deal Town 3 – 0 Metropolitan Police (Hayes) Slade Green Athletic 0 – 2 Tunbridge Wells Thames Polytechnic 0– 1 Herne Bay Ramsgate 2 – 5 (aet) Alma Swanley Hythe Town 1 – 2 Crockenhill First Round Cray Wanderers 2 – 2 (aet) Metropolitan Police (Hayes) Replay 1: Metropolitan Police (Hayes) 3 – 3 (aet) Cray Wanderers Replay 2: Metropolitan Police (Hayes) 1 – 1 (aet) Cray Wanderers; Metropolitan Police (Hayes) won 4–3 on penalties Kent Police 0 – 1 Hythe Town
Sources: 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 mostly 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 eighteen clubs (including one non-reserve team, Snowdown Colliery Welfare), sixteen of which had competed in the division the previous season together with two additional clubs Dover Athletic R Thames Polytechnic R
The division was won for the second occasion in three seasons by Fisher Athletic R who pipped Sheppey United R to the top position by goal difference only.
After the end of the season both Canterbury City R and Chatham Town R resigned from the division.
League Table
Division Two Cup The 1985–86 Kent Football League Division Two Cup was won by Faversham Town R.
The competition, contested by all eighteen clubs in the division, comprised five single match tie rounds (with the first round featuring two ties) culminating in the final which was played on a neutral ground (at Ramsgate F.C. this season).
Quarter-finals, Semi-finals and Final
<onlyinclude> Second Round Sheppey United R 3 – 0 Ashford Town R Thames Polytechnic R 0 – 1 Fisher Athletic R Canterbury City R 0 – 5 Deal Town R Snowdown Colliery Welfare 1 – 3 Thanet United R Sittingbourne R 0 – 1 Erith & Belvedere R Herne Bay R 2 – 1 Darenth Heathside R Whitstable Town R 1– 3 (aet) Faversham Town R Dover Athletic R 1 – 2 Chatham Town R First Round Herne Bay R 1 – 0 Folkestone R Chatham Town R 2 – 1 Hythe Town R Sources: Final: Semi-finals: Quarter-finals: ; ; Second Round:; ; ; First Round: ;
References