| ROUND | R1 | R2 | R3 | R4 | QF | SF | F | |
| l1 | l2 | |||||||
| Season archive |
| Tuesday, 23 September 2008 | ||||||
| r3 | Burnley | 1-0 | Fulham | |||
| 88 | Rodriguez | |||||
| r3 | Leeds United | 3-2 | Hartlepool United | |||
| 14 | Snodgrass | 2 | Monkhouse | |||
| 58 | Showunmi | 33 | Porter | |||
| 90 | Robinson | |||||
| r3 | Sunderland | 2-2 | Northampton Town | aet, p4-3 | ||
| 86 | Stokes | 20 | Larkin | |||
| 90 | Stokes | 81 | Guttridge | |||
| r3 | Swansea City | 1-0 | Cardiff City | |||
| 57 | Jordi Gómez | |||||
| r3 | Arsenal | 6-0 | Sheffield United | |||
| 31 | Bendtner | |||||
| 42 | Bendtner | |||||
| 44 | Vela | |||||
| 50 | Vela | |||||
| 57 | Wilshere | |||||
| 87 | Vela | |||||
| r3 | Liverpool | 2-1 | Crewe Alexandra | |||
| 15 | Agger | 25 | O'Connor | |||
| 58 | Lucas | |||||
| r3 | Manchester United | 3-1 | Middlesbrough | |||
| 25 | Ronaldo | 56 | Johnson | |||
| 79 | Giggs | |||||
| 90 | Nani | |||||
| r3 | Rotherham United | 3-1 | Southampton | |||
| 20 | Fenton | 61 | John | |||
| 56 | Harrison | |||||
| 69 | Broughton | |||||
| r3 | Stoke City | 2-2 | Reading | aet, p4-3 | ||
| 9 | Péricard | 45(p) | Henry | |||
| 50 | Sidibé | 75 | Henry | |||
| r3 | Watford | 1-0 | West Ham United | |||
| 70(og) | Mullins | |||||
| Wednesday, 24 September 2008 | ||||||
| r3 | Aston Villa | 0-1 | QPR | |||
| 58 | Stewart | |||||
| r3 | Blackburn Rovers | 1-0 | Everton | |||
| 10 | Olsson | |||||
| r3 | Ipswich Town | 1-4 | Wigan Athletic | |||
| 61 | Walters | 52 | Cattermole | |||
| 64 | Kapo | |||||
| 70 | Scharner | |||||
| 90 | Camara | |||||
| r3 | Newcastle United | 1-2 | Tottenham Hotspur | |||
| 90 | Owen | 62 | Pavlyuchenko | |||
| 66 | O'Hara | |||||
| r3 | Portsmouth | 0-4 | Chelsea | |||
| 36(p) | Lampard | |||||
| 45 | Malouda | |||||
| 49 | Lampard | |||||
| 64 | Kalou | |||||
| Tuesday, 4 November 2008 | ||||||
| r3 | Brighton & HA | 1-4 | Derby County | |||
| 36 | Elphick | 28 | Villa | |||
| 34 | Ellington | |||||
| 73 | Villa | |||||
| 87 | Villa | |||||
| 4 | +2 | James HENRY (Reading, 1p) |
| Jermaine BECKFORD (Leeds United) | ||
| +1 | Nathan ELLINGTON (Derby County) | |
| Martin PATERSON (Burnley) | ||
| 3 | +1 | Joel PORTER (Hartlepool United) |
| Rob EARNSHAW (Nottingham Forest) | ||
| +1 | Henri CAMARA (Wigan Athletic) | |
| Emmanuel LEDESMA (QPR) | ||
| +3 | Carlos VELA (Arsenal) | |
| +3 | Emanuel VILLA (Derby County) |