The division featured 17 clubs, 16 of which competed in the previous season together with one additional club: At the end of the season three clubs left the division: The 2008–09 Kent Football League Challenge Cup, known as the Bulmers Cider Kent League Cup (reflecting the sponsorship by Bulmers), was won by Croydon.
The competition was contested by the 17 teams from the Premier Division over a total of five rounds: four on an aggregate basis (home and away matches) followed by a final match played on a neutral ground (at Welling United F.C.
At the end of the season Folkestone Invicta R and Sevenoaks Town R were relegated and Dover Athletic R left the league.
The division featured eleven clubs, nine of which competed in the previous season together with two additional clubs: At the end of the season Herne Bay R and Holmedale R were promoted to Division One and Greenwich Borough R, Tunbridge Wells R and Welling United R left the league.
this season) Byes for the remaining nine teams Source: SCEFL Archives