| N | Torneo | Jornada | Fecha | Local | Result. | Visita | Estadio | Arbitro | Público | Fuente | Obs |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | FA Cup 2008/09 | First Round Proper - 1 | 08/11/2008 | Brighton & Hove Albion | 3 - 3 | Hartlepool United | [33] | ||||
| 2 | FA Cup 2008/09 | First Round Proper - 2 | 18/11/2008 | Hartlepool United | 2 - 1 | Brighton & Hove Albion | [33] | ||||
| 3 | FA Cup 2008/09 | Second Round Proper - 1 | 29/11/2008 | Fleetwood Town | 2 - 3 | Hartlepool United | [33] | ||||
| 4 | FA Cup 2008/09 | Third Round Proper - 1 | 03/01/2009 | Hartlepool United | 2 - 0 | Stoke City | [33] | ||||
| 5 | FA Cup 2008/09 | Fourth Round Proper - 1 | 24/01/2009 | Hartlepool United | 0 - 2 | West Ham United | [33] |
