1999–2000 FA Cup Calendar Calendar

| Round | Date_ | Matches | Clubs | New_entries_this_round | Prize_money |
|---|---|---|---|---|---|
| Third Round Proper | 10 December 1999 | 32 | 64 → 32 | 43: 2nd–44th | £40,000 |
| Fourth Round Proper | 8 January 2000 | 16 | 32 → 16 | none | £60,000 |
| Fifth Round Proper | 29 January 2000 | 8 | 16 → 8 | none | £120,000 |
| Sixth Round Proper | 19 February 2000 | 4 | 8 → 4 | none | £300,000 |
| Semi Finals | 2 April 2000 | 2 | 4 → 2 | none | £900,000 |
| Final | 20 May 2000 | 1 | 2 → 1 | none | £1,000,000 |