1988–89 Kent Football League

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The 1988–89 Kent Football League season (known as the Winstonlead Kent League for sponsorship reasons) was the twenty-third 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 clubs, nineteen of which competed in the previous season together with one additional club:
 * Chatham Town, relegated from the Southern League

The league was won, for the first occasion by Hythe Town - whose reserves team completed a Division Two league and cup double.

At the end of the season champions Hythe Town were promoted to the Southern League Southern Division and both bottom clubs, Chatham Town and Herne Bay, were re-elected to continue their membership of the division.

Challenge Cup
The 1988–89 Kent Football League Challenge Cup was won, for the only occasion in their history, by Alma Swanley.

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

Second Round

 * Slade Green 2 – 5 Whitstable Town
 * Hythe Town 3 – 0 Kent Police
 * Herne Bay 0 – 2 Alma Swanley
 * Tunbridge Wells 1 – 0 Thames Polytechnic
 * Deal Town 4 – 2 Darenth Heathside
 * Metropolitan Police (Hayes) 0 – 3 Greenwich Borough
 * Crockenhill 0 – 2 Ramsgate
 * Danson 1 – 0 Beckenham Town

First Round
Sources:
 * Darenth Heathside 2 – 1 Cray Wanderers
 * Metropolitan Police (Hayes) 4 – 3 Chatham Town
 * Crockenhill 3 – 0 Faversham Town
 * Sittingbourne 1 – 2 Danson
 * Byes for the other twelve 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 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 nineteen clubs including one non-reserve team, Snowdown Colliery Welfare for their final season in the league; sixteen of the clubs had competed in the division the previous season together with three additional clubs:
 * Chatham Town R
 * Cray Wanderers R
 * Greenwich Borough R

The division was won by a resurgent Hythe Town R - who had been re-elected to the league after ending the previous season in the bottom two – part of a league and cup double.

At the end of the season: Chatham Town R, Deal Town R and champions Hythe Town R withdrew from the division; Snowdown Colliery Welfare, who were founder members of the league in 1966, had their registration cancelled by the League as the club no longer held the league requirement of Senior status - the Kent County FA had, owing to the club's long spell of ten seasons in Division Two, ruled the club of Intermediate status; bottom club Herne Bay were re-elected to continue their membership of the division.

Division Two Cup
The 1988–89 Kent Football League Division Two Cup was won by Hythe Town R part of a league and cup double.

The competition, contested by all nineteen clubs in the division, comprised five single match tie rounds (with the first round featuring three ties) culminating in the final (played at Hythe Town F.C.). this season).

Second Round

 * Thames Polytechnic R 0 – 2 Hythe Town R
 * Sheppey United R 2 – 1 Snowdown Colliery Welfare
 * Hastings Town R 0– 0 Ashford Town R
 * Replay: Ashford Town R v Hastings Town R
 * Beckenham Town R 0 – 5 Cray Wanderers R
 * Chatham Town R 4 – 2 Ramsgate R
 * Sittingbourne R 1 – 2 Greenwich Borough R
 * Deal Town R W – x Faversham Town R (Match awarded to Deal Town R)
 * Dover Athletic R 0 – 1 Folkestone R

First Round
Sources:
 * Thanet United R 0 – 5 Sheppey United R
 * Herne Bay R 1 – 7 Hastings Town R
 * Dover Athletic R 4 – 1 Whitstable Town R
 * Byes for the other thirteen clubs
 * Final:
 * Semi-finals: ;
 * Quarter-finals: ; ; ;
 * Second Round: ; ; ;
 * First Round: ; ;