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FA Cup
Below are the FA Cup results for the Second Round proper for the 1999-2000 season.
| Second Round | Score | |
| Blackpool | Hendon | 2-0 |
| Bournemouth | Bristol City | 0-2 |
| Burnley | Rotherham United | 2-0 |
| Bury | Cardiff City | 0-0 |
| Cambridge United | Bamber Bridge | 1-0 |
| Exeter City | Aldershot Town | 2-0 |
| Forest Green Rovers | Torquay United | 0-3 |
| Gillingham | Darlington | 3-1 |
| Hayes | Hull City | 2-2 |
| Hereford United | Hartlepool United | 1-0 |
| Ilkeston Town | Rushden & Diamonds | 1-1 |
| Luton Town | Lincoln City | 2-2 |
| Oldham Athletic | Swansea City | 1-0 |
| Plymouth Argyle | Brighton & Hove Albion | 0-0 |
| Preston North End | Enfield | 0-0 |
| Reading | Halifax Town | 1-1 |
| Shrewsbury Town | Oxford United | 2-2 |
| Stalybridge Celtic | Chester City | 1-2 |
| Wrexham | Rochdale | 2-1 |
| Wycombe Wanderers. | Wigan Athletic | 2-2 |
| Second Round Replays | Score | |
| Brighton & Hove Albion | Plymouth Argyle |
1-2 |
| Cardiff City | Bury |
1-0 |
| Enfield | Preston North End |
0-3 |
| Halifax Town | Reading |
0-1 |
| Hull City | Hayes |
3-2 |
| Lincoln City | Luton Town |
0-1 |
| Oxford United | Shrewsbury Town |
2-1 |
| Rushden & Diamonds | Ilkeston Town | 3-0 |
| Wigan Athletic | Wycombe Wanderers | 2-1 |