2008–09 FA Cup Calendar Calendar

| Round | Main_date | Number_of_fixtures | Clubs | New_entries_this_round | Prize_money |
|---|---|---|---|---|---|
| Second Round Proper | 29 November 2008 | 20 | 84 → 64 | none | £30,000 |
| Third Round Proper | 3 January 2009 | 32 | 64 → 32 | 44: 1st–44th | £75,000 |
| Fourth Round Proper | 24 January 2009 | 16 | 32 → 16 | none | £100,000 |
| Fifth Round Proper | 14 February 2009 | 8 | 16 → 8 | none | £200,000 |
| Sixth Round Proper | 7 March 2009 | 4 | 8 → 4 | none | £400,000 |
| Semi-Finals | 18 April 2009 19 April 2009 | 2 | 4 → 2 | none | Winners: £1,000,000 Losers: £500,000 |
| Final | 30 May 2009 | 1 | 2 → 1 | none | Winner: £2,000,000 Loser: £1,000,000 |