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FA Cup
Below are the FA Cup results for the Fourth Round for the 1999-2000 season. Games played on the weekend of January 8 and 9.
| Fourth Round | Score | |
| Arsenal | Leicester City |
0-0 |
| Aston Villa | Southampton | 1-0 |
| Charlton Athletic | Queens Park Rangers | 1-0 |
| Chelsea | Nottingham Forest | 2-0 |
| Coventry City | Burnley | 3-0 |
| Everton | Birmingham City | 2-0 |
| Fulham | Wimbledon | 3-0 |
| Gillingham | Bradford City | 3-1 |
| Grimsby Town | Bolton Wanderers | 0-2 |
| Liverpool | Blackburn Rovers | 0-1 |
| Manchester City | Leeds United | 2-5 |
| Newcastle United | Sheffield United | 4-1 |
| Plymouth Argyle | Preston North End | 0-3 |
| Sheffield Wednesday | Wolverhampton Wanderers | 1-1 |
| Tranmere Rovers | Sunderland | 1-0 |
| Wrexham | Cambridge United | 1-2 |
| Fourth Round Replay | Score | |
| Leicester City | Arsenal |
0-0 aet |
|
Leicester City Win 6-5 on Penalties |
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| Wolverhampton Wanderers | Sheffield Wednesday | 0-0 aet |
|
Sheffield Wednesday Win 4-3 on Penalties |
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