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FA Cup
Below are the FA Cup results for the First Round proper for the 1999-2000 season.
| First Round | Score | |
| Rushden & Diamonds | Scunthorpe United | 2-0 |
| Aldershot Town | Hednesford Town | 1-1 |
| Barnet | Burnley | 0-1 |
| Bath City | Hendon | 2-0 |
| Blackpool | Stoke City | 2-0 |
| Brentford | Plymouth Argyle | 2-2 |
| Bristol City | Mansfield Town | 3-2 |
| Bristol Rovers | Preston North End | 0-1 |
| Burton Albion | Rochdale | 0-0 |
| Cambridge City | Wigan Athletic | 0-2 |
| Cambridge United | Gateshead | 0-2 |
| Cheltenham Town | Gillingham | 1-1 |
| Chesterfield | Enfield | 1-2 |
| Darlington | Southport | 2-1 |
| Doncaster Rovers | Halifax Town | 0-2 |
| Exeter City | Eastwood Town | 2-1 |
| Forest Green Rovers | Guiseley | 6-0 |
| Hartlepool | Milwall | 1-0 |
| Hayes | Runcorn | 2-1 |
| Hereford United | York City | 1-0 |
| Ilkeston Town | Carlisle United | 2-1 |
| Leyton Orient | Cardiff City | 1-1 |
| Lincoln City | Welling United | 1-0 |
| Luton Town | Kingstonian | 4-2 |
| Macclesford Town | Hull City | 0-0 |
| Merthyr Tydfil | Stalybridge Celtic | 2-2 |
| Notts County | Bournemouth | 1-1 |
| Oldham Athletic | Chelmsford City | 4-0 |
| Oxford United | Morecambe | 3-2 |
| Peterborough United | Brighton & Hove Albion | 1-1 |
| Reading | Yeovil Town | 4-2 |
| Rotherham United | Worthing | 3-0 |
| Shrewsbury Town | Northampton Town | 2-1 |
| St Albans City | Bamber Bridge | 0-2 |
| Swansea City | Colchester United | 2-1 |
| Tamworth | Bury | 2-2 |
| Torquay United | Southend United | 1-0 |
| Whyteleafe | Chester City | 0-0 |
| Wrexham | Kettering Town | 1-1 |
| Wycome Wanderers | Oxford City | 1-1 |
| First Round Replays | Score | |
| Bournemouth | Notts County | 4-3 |
| Brighton & Hove Albion | Peterborough United | 3-0 |
| Bury | Tamworth | 2-1 |
| Cardiff City | Leyton Orient | 3-1 |
| Chester City | Whyteleafe | 3-1 |
| Gillingham | Cheltenham Town | 3-2 |
| Hednesford Town | Aldershot Town | 1-2 |
| Hull City | Macclesford Town | 4-0 |
| Kettering Town | Wrexham | 0-2 |
| Oxford City | Wycome Wanderers | 1-1* |
| Plymouth Argyle | Brentford | 2-1 |
| Rochdale | Burton Albion | 3-0 |
| Staylebridge Celtic | Merthyr Tydfil | 3-1 |
* Match Abandoned due to fire alarm.
| First Round, Second Replay | Score | |
| Oxford City | Wycome Wanderers | 0-1 |