2008–09 FA Trophy Calendar Calendar

| Round | Date_ | Matches | Clubs | New_entries_this_round | Prize_money |
|---|---|---|---|---|---|
| Preliminary Round | 4 October 2008 | 51 | 263→212 | 102 | £1,000 |
| First Round Qualifying | 18 October 2008 | 72 | 212→140 | 93 | £2,300 |
| Second Round Qualifying | 1 November 2008 | 36 | 140→104 | none | £3,000 |
| Third Round Qualifying | 22 November 2008 | 40 | 104→64 | 44 | £4,000 |
| First Round | 13 December 2008 | 32 | 64→32 | 24 | £5,000 |
| Second Round | 10 January 2009 | 16 | 32→16 | none | £6,000 |
| Third Round | 31 January 2009 | 8 | 16→8 | none | £7,000 |
| Fourth Round | 21 February 2009 | 4 | 8→4 | none | £8,000 |
| Semi-finals | 14 March and 21 March 2009 | 2 | 4→2 | none | £16,000 |
| Final | 9 May 2009 | 1 | 2 → 1 | none | Winner: £50,000 Loser: £25,000 |