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FA Cup
Below are the FA Cup results for the Fifth Round for the 1999-2000 season.
| Fifth Round | Score | |
| Aston Villa | Leeds United | 3-2 |
| Blackburn Rovers | Newcastle United | 1-2 |
| Cambridge United | Bolton Wanderers | 1-3 |
| Chelsea | Leicester City | 2-1 |
| Coventry City | Charlton Athletic | 2-3 |
| Everton | Preston North End | 2-0 |
| Fulham | Tranmere Rovers | 1-2 |
| Gillingham | Sheffield Wednesday | 3-1 |