| N | Torneo | Jornada | Fecha | Local | Result. | Visita | Estadio | Arbitro | Público | Fuente | Obs |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | FA Cup 1999/00 | Third Round Proper - 1 | 11/12/1999 | Hull City | 1 - 6 | Chelsea | [33] | ||||
| 2 | FA Cup 1999/00 | Fourth Round Proper - 1 | 19/01/2000 | Chelsea | 2 - 0 | Nottingham Forest | [33] | ||||
| 3 | FA Cup 1999/00 | Fifth Round Proper - 1 | 31/01/2000 | Chelsea | 2 - 1 | Leicester City | [33] | ||||
| 4 | FA Cup 1999/00 | Sixth Round Proper - 1 | 20/02/2000 | Chelsea | 5 - 0 | Gillingham | [33] | ||||
| 5 | FA Cup 1999/00 | Semifinal - 1 | 09/04/2000 | Chelsea | 2 - 1 | Newcastle United | Wembley (original), London | 73876 | [33] | ||
| 6 | FA Cup 1999/00 | Final - 1 | 20/05/2000 | Chelsea | 1 - 0 | Aston Villa | Wembley (original), London | 78217 | [33] |
