2008–09 FA Cup Calendar Calendar

| Round | Main_date | Number_of_fixtures | Clubs | New_entries_this_round | Prize_money |
|---|---|---|---|---|---|
| Extra Preliminary Round | 16 August 2008 | 203 | 761 → 558 | 406: 356th–761st | £750 |
| Preliminary Round | 30 August 2008 | 166 | 558 → 392 | 129: 227th–355th | £1,500 |
| First Round Qualifying | 13 September 2008 | 116 | 392 → 276 | 66: 161st–226th | £3,000 |
| Second Round Qualifying | 27 September 2008 | 80 | 276 → 196 | 44: 117th–160th | £4,500 |
| Third Round Qualifying | 11 October 2008 | 40 | 196 → 156 | none | £7,500 |
| Fourth Round Qualifying | 25 October 2008 | 32 | 156 → 124 | 24: 93rd–116th | £12,500 |
| First Round Proper | 8 November 2008 | 40 | 124 → 84 | 48: 45th–92nd | £20,000 |