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