Dover Athletic became champions five games before the end of the season and were promoted to the Conference South along with play-off winners Staines Town. Harlow Town, Heybridge Swifts and Ramsgate were relegated to the Division One sections, while Margate, who also finished in the relegation zone, were reprieved due to the demotion of clubs higher up the pyramid.
Source:[1][2] Rules for classification: 1) points; 2) goal difference; 3) number of goals scored. Notes:
^Harlow Town were deducted three points for fielding an ineligible player against Wealdstone on 14 February 2009 (2–1).
^Ramsgate were deducted four points for playing more than permitted number of short term loan players in three matches, including Margate on 27 December 2008 (2–0) and Tonbridge Angels on 3 January 2009 (2–2).
Aveley won the division and were promoted to the Premier Division along with play-off winners Waltham Abbey. Witham Town and Hillingdon Borough finished in the bottom two places and left the league.
Kingstonian won the division and were promoted to the Premier Division along with play-off winners Cray Wanderers. Crowborough Athletic finished bottom of the table and returned to the Sussex County League after only one season in the Isthmian League. Chipstead were reprieved from relegation due to the demotion of clubs higher up the pyramid.
TheIsthmian League Cup 2008–09 was the 35th season of theIsthmian League Cup, the league cup competition of theIsthmian League. Sixty-six clubs took part. The competition commenced on 18 November 2008 and finished on 8 April 2009.[4]