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FA Cup
Below are the FA Cup results for the Third Round for the 1999-2000 season.
| Third Round | Score | |
| Aston Villa | Darlington* | 2-1 |
| Arsenal | Blackpool | 3-1 |
| Bolton Wanderers | Cardiff City | 1-0 |
| Cambridge United | Crystal Palace | 2-0 |
| Charlton Athletic | Swindon Town | 2-1 |
| Chester City | Manchester City | 1-4 |
| Crewe Alexander | Bradford City | 1-2 |
| Derby County | Burnley | 0-1 |
| Exeter City | Everton | 0-0 |
| Fulham | Luton Town | 2-2 |
| Grimsby Town | Stockport County | 3-2 |
| Hull City | Chelsea | 1-6 |
| Hereford United | Leicester City | 0-0 |
| Huddersfield Town | Liverpool | 0-2 |
| Ipswich Town | Southampton | 0-1 |
| Leeds United | Port Vale | 2-0 |
| Norwich City | Coventry City | 1-3 |
| Nottingham Forest | Oxford United | 1-1 |
| Preston North End | Oldham Athletic | 2-1 |
| Queens Park Rangers | Torquay United | 1-1 |
| Reading | Plymouth Argyle | 1-1 |
| Sheffield United | Rushden & Diamonds | 1-1 |
| Sheffield Wednesday | Bristol City | 1-0 |
| Sunderland | Portsmouth | 1-0 |
| Tottenham Hotspur | Newcastle United | 1-1 |
| Tranmere Rovers | West Ham United | 1-0 |
| Walsall | Gillingham | 1-1 |
| Watford | Birmingham City | 0-1 |
| West Bromwich Albion | Blackburn Rovers | 2-2 |
| Wimbledon | Barnsley | 1-0 |
| Wrexham | Middlesbrough | 2-1 |
| Wigan Athletic | Wolverhampton Wanderers | 0-1 |
* Lucky Loser.
| Third Round Replay | Score | |
| Blackburn Rovers | West Bromwich Albion |
2-0 aet |
| Everton | Exeter City |
1-0 |
| Gillingham | Walsall | 2-1 |
| Leicester City | Hereford United |
2-1 aet |
| Luton Town | Fulham | 0-3 |
| Newcastle United | Tottenham Hotspur | 6-1 |
| Oxford United | Nottingham Forest | 1-3 |
| Plymouth Argyle | Reading | 1-0 |
| Rushden & Diamonds | Sheffield United | 1-1 |
|
Sheffield United win 6-5 on Penalties |
||
| Torquay United | Queens Park Rangers | 2-3 |