1999–2000 FA Cup Calendar Calendar

| Round | Date_ | Matches | Clubs | New_entries_this_round | Prize_money |
|---|---|---|---|---|---|
| Preliminary Round | 21 August 1999 | 166 | 558 → 392 | 161: 227th–387th | £1,000 |
| First Round Qualifying | 4 September 1999 | 116 | 392 → 276 | 66: 161st–226th | £2,250 |
| Second Round Qualifying | 18 September 1999 | 80 | 276 → 196 | 44: 117th–160th | £3,750 |
| Third Round Qualifying | 2 October 1999 | 40 | 196 → 156 | none | £5,000 |
| Fourth Round Qualifying | 16 October 1999 | 32 | 156 → 124 | 24: 93rd–116th | £10,000 |
| First Round Proper | 30 October 1999 | 40 | 124 → 84 | 48: 45th–92nd | £16,000 |
| Second Round Proper | 19 October 1999 | 20 | 84 → 64 | none | £24,000 |