| N | Torneo | Jornada | Fecha | Local | Result. | Visita | Estadio | Arbitro | Público | Fuente | Obs |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | FA Cup 1999/00 | Third Round Proper - 1 | 11/12/1999 | Hereford United | 0 - 0 | Leicester City | [33] | ||||
| 2 | FA Cup 1999/00 | Third Round Proper - 2 | 22/12/1999 | Leicester City | 2 - 1 | Hereford United | [33] | [1]a | |||
| 3 | FA Cup 1999/00 | Fourth Round Proper - 1 | 09/01/2000 | Arsenal | 0 - 0 | Leicester City | [33] | ||||
| 4 | FA Cup 1999/00 | Fourth Round Proper - 2 | 19/01/2000 | Leicester City | 0 - 0 (6-5) | Arsenal | [33] | [2]a | |||
| 5 | FA Cup 1999/00 | Fifth Round Proper - 1 | 31/01/2000 | Chelsea | 2 - 1 | Leicester City | [33] |
