2008–09 Conference League Cup Calendar Calendar

| Round | Date_ | Matches | Clubs | New_entries_this_round | Prize_money |
|---|---|---|---|---|---|
| First Round | 8 September 2008 | 22 | 68 → 46 | 44 | £2,000 |
| Second Round | 6 October 2008 | 14 | 46 → 32 | 6 | £3,000 |
| Third Round | 4 November 2008 | 16 | 32 → 16 | 18 | £3,500 |
| Fourth Round | 2 December 2008 | 8 | 16 → 8 | none | £4,500 |
| Quarter-finals | 12 January 2009 | 4 | 8 → 4 | none | £7,000 |
| Semi-finals | 2009 | 2 | 4 → 2 | none | £10,000 |
| Final | 2009 | 1 | 2 → 1 | none | Winner: £16,000; Loser: £8,000 |