| N | Torneo | Jornada | Fecha | Local | Result. | Visita | Estadio | Arbitro | Público | Fuente | Obs |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | FA Cup 1999/00 | First Round Proper - 1 | 30/10/1999 | Brentford | 2 - 2 | Plymouth Argyle | [33] | ||||
| 2 | FA Cup 1999/00 | First Round Proper - 2 | 09/11/1999 | Plymouth Argyle | 2 - 1 | Brentford | [33] | [1]a | |||
| 3 | FA Cup 1999/00 | Second Round Proper - 1 | 20/11/1999 | Plymouth Argyle | 0 - 0 | Brighton & Hove Albion | [33] | ||||
| 4 | FA Cup 1999/00 | Second Round Proper - 2 | 30/11/1999 | Brighton & Hove Albion | 1 - 2 | Plymouth Argyle | [33] | ||||
| 5 | FA Cup 1999/00 | Third Round Proper - 1 | 11/12/1999 | Reading | 1 - 1 | Plymouth Argyle | [33] | ||||
| 6 | FA Cup 1999/00 | Fourth Round Proper - 1 | 08/01/2000 | Plymouth Argyle | 0 - 3 | Preston North End | [33] |
