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.
The Isthmian League Cup 2008–09 was the 35th season of the Isthmian League Cup, the league cup competition of the Isthmian League. Sixty-six clubs took part. The competition commenced on 18 November 2008 and finished on 8 April 2009.[4]
Calendar
Round
Dates
Matches
Clubs
First round
18 November 2008
2
66 → 64
Second round
25 November 2008 to 20 January 2009
32
64 → 32
Third round
7 January 2009 to 27 January 2009
16
32 → 16
Fourth round
27 January 2009 to 24 February 2009
8
16 → 8
Quarterfinals
24 February 2009 to 4 March 2009
4
8 → 4
Semifinals
17 March 2009
2
4 → 2
Final
8 April 2009
1
2 → 1
Fixtures and results
Fixtures are listed in alphabetical order, not that which they were drawn in.
First round
Four clubs from division Ones participated in the first round, while all other clubs received a bye to the second round.