| N | Torneo | Jornada | Fecha | Local | Result. | Visita | Estadio | Arbitro | Público | Fuente | Obs |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | FA Cup 1999/00 | First Round Proper - 1 | 30/10/1999 | Cambridge United | 1 - 0 | Gateshead | [33] | ||||
| 2 | FA Cup 1999/00 | Second Round Proper - 1 | 20/11/1999 | Cambridge United | 1 - 0 | Bamber Bridge | [33] | ||||
| 3 | FA Cup 1999/00 | Third Round Proper - 1 | 10/12/1999 | Cambridge United | 2 - 0 | Crystal Palace | [33] | ||||
| 4 | FA Cup 1999/00 | Fourth Round Proper - 1 | 08/01/2000 | Wrexham | 1 - 2 | Cambridge United | [33] | ||||
| 5 | FA Cup 1999/00 | Fifth Round Proper - 1 | 29/01/2000 | Cambridge United | 1 - 3 | Bolton Wanderers | [33] |
