| League Cup Matches |
| |  | | | |
| 19 Aug 2008: Round 1
|
| Accrington | | 0 - 1 | | Brentford |
| Barnet | | 1 - 2 | | Burnley |
| Barnsley | | 0 - 0 | | Plymouth Argyle |
| | (5 - 4 pen.) | |
| Blackpool | | 4 - 2 | | Peterborough |
| Bournemouth | | 0 - 0 | | Boston |
| | (2 - 3 pen.) | |
| Bristol City | | 1 - 3 | | Tranmere Rovers |
| Cheltenham Town | | 3 - 1 | | Bury |
| Chesterfield | | 2 - 4 | | Wycombe |
| Colchester Utd | | 1 - 0 | | Bristol Rovers |
| Crewe | | 1 - 0 | | Swindon Town |
| Darlington | | 0 - 4 | | Nott. Forest |
| Doncaster | | 0 - 1 | | Chester |
| Hartlepool | | 0 - 0 | | Bradford City |
| | (3 - 0 pen.) | |
| Hereford | | 2 - 1 | | Lincoln City |
| Huddersfield | | 1 - 0 | | Grimsby Town |
| Ipswich Town | | 2 - 0 | | Notts County |
| Macclesfield | | 2 - 0 | | Southend United |
| Mansfield Town | | 1 - 2 | | Carlisle United |
| Northampton | | 0 - 0 | | Torquay |
| | (4 - 3 pen.) | |
| Oldham Athletic | | 3 - 1 | | Walsall |
| Port Vale | | 0 - 2 | | Millwall |
| Rochdale | | 0 - 2 | | Cardiff City |
| Rotherham | | 3 - 2 | | MK Dons |
| Scunthorpe Utd | | 0 - 0 | | Leyton Orient |
| | (4 - 2 pen.) | |
| Shrewsbury | | 0 - 1 | | Brighton |
| Stockp. County | | 1 - 1 | | Wrexham |
| | (5 - 4 pen.) | |
| Swansea City | | 0 - 1 | | Gillingham |
| Yeovil | | 0 - 1 | | QPR |
| | | | | |
| 9 Sep 2008: Round 2
|
| Arsenal | | 1 - 2 | | Wycombe |
| Aston Villa | | 0 - 1 | | Blackpool |
| Barnsley | | 0 - 0 | | Portsmouth |
| | (4 - 5 pen.) | |
| Brentford | | 0 - 2 | | Sheffield Utd |
| Brighton | | 3 - 1 | | Sheff Wed |
| Charlton | | 3 - 0 | | Millwall |
| Chelsea | | 2 - 1 | | Huddersfield |
| Chester | | 0 - 2 | | Liverpool |
| Colchester Utd | | 3 - 2 | | Blackburn |
| Coventry City | | 1 - 0 | | Bolton |
| Crewe | | 1 - 0 | | Manchester Utd |
| Crystal Palace | | 1 - 0 | | Rotherham |
| Derby County | | 3 - 0 | | Ipswich Town |
| Everton | | 1 - 2 | | Boston |
| Hull City | | 0 - 1 | | Cardiff City |
| Leicester City | | 2 - 1 | | West Brom |
| Macclesfield | | 0 - 0 | | Stoke City |
| | (3 - 0 pen.) | |
| Manchester City | | 1 - 0 | | Fulham |
| Newcastle | | 4 - 0 | | QPR |
| Norwich | | 0 - 1 | | Hereford |
| Oldham Athletic | | 0 - 0 | | Luton Town |
| | (3 - 4 pen.) | |
| Preston | | 2 - 0 | | Gillingham |
| Reading | | 1 - 3 | | Birmingham |
| Southampton | | 2 - 0 | | Northampton |
| Stockp. County | | 1 - 2 | | Middlesbrough |
| Sunderland | | 2 - 0 | | Cheltenham Town |
| Tottenham | | 2 - 0 | | Scunthorpe Utd |
| Tranmere Rovers | | 0 - 2 | | Leeds United |
| Watford | | 1 - 3 | | Nott. Forest |
| West Ham | | 4 - 0 | | Hartlepool |
| Wigan Athletic | | 2 - 0 | | Carlisle United |
| Wolverhampton | | 0 - 0 | | Burnley |
| | (4 - 2 pen.) | |
| | | | | |
| 14 Oct 2008: Round 3
|
| Birmingham | | 1 - 2 | | Manchester City |
| Boston | | 1 - 2 | | Blackpool |
| Cardiff City | | 0 - 1 | | Southampton |
| Colchester Utd | | 1 - 3 | | Brighton |
| Coventry City | | 0 - 1 | | Leicester City |
| Crewe | | 0 - 0 | | Derby County |
| | (4 - 5 pen.) | |
| Hereford | | 2 - 4 | | West Ham |
| Luton Town | | 1 - 0 | | Leeds United |
| Middlesbrough | | 3 - 2 | | Wigan Athletic |
| Nott. Forest | | 1 - 2 | | Crystal Palace |
| Preston | | 2 - 2 | | Chelsea |
| | (3 - 2 pen.) | |
| Sheffield Utd | | 0 - 0 | | Newcastle |
| | (4 - 5 pen.) | |
| Sunderland | | 0 - 0 | | Portsmouth |
| | (2 - 4 pen.) | |
| Tottenham | | 3 - 0 | | Liverpool |
| Wolverhampton | | 1 - 1 | | Charlton |
| | (4 - 3 pen.) | |
| Wycombe | | 0 - 1 | | Macclesfield |
| | | | | |
| 4 Nov 2008: Round 4
|
| Blackpool | | 0 - 2 | | Luton Town |
| Derby County | | 0 - 1 | | Southampton |
| Leicester City | | 1 - 2 | | Manchester City |
| Macclesfield | | 1 - 0 | | Preston |
| Newcastle | | 0 - 1 | | Brighton |
| Tottenham | | 1 - 2 | | Crystal Palace |
| West Ham | | 1 - 0 | | Portsmouth |
| Wolverhampton | | 0 - 3 | | Middlesbrough |
| | | | | |
| 16 Dec 2008: Quarter-Final
|
| Luton Town | | 0 - 1 | | Crystal Palace |
| Macclesfield | | 1 - 2 | | Middlesbrough |
| Manchester City | | 0 - 2 | | Southampton |
| West Ham | | 0 - 1 | | Brighton |
| | | | | |
| 13 Jan 2009: Semi-Final, Leg 1
|
| Brighton | | vs. | | Crystal Palace |
| Middlesbrough | | vs. | | Southampton |
| | | | | |
| 20 Jan 2009: Semi-Final, Leg 2
|
| Crystal Palace | | (0 - 0 agg.) | | Brighton |
| Southampton | | (0 - 0 agg.) | | Middlesbrough |
| | | | | |
| 1 Feb 2009: Final
|
| [TBD] | | vs. | | [TBD] |