| League Cup Matches |
| |  | | | |
| 18 Aug 2009: Round 1
|
| Blackpool | | 1 - 0 | | Rochdale |
| Boston | | 0 - 3 | | Oldham Athletic |
| Bournemouth | | 3 - 0 | | Cambridge |
| Brighton | | 2 - 0 | | Torquay |
| Bristol Rovers | | 1 - 0 | | Stockport County |
| Burnley | | 0 - 0 | | Bury |
| | (3 - 2 pen.) | |
| Cheltenham Town | | 0 - 0 | | Tranmere Rovers |
| | (4 - 2 pen.) | |
| Chesterfield | | 1 - 0 | | Brentford |
| Chester | | 2 - 1 | | Wycombe |
| Colchester United | | 0 - 2 | | Bradford City |
| Coventry City | | 2 - 0 | | Sheff Wed |
| Crewe | | 1 - 1 | | Swansea City |
| | (3 - 0 pen.) | |
| Gillingham | | 2 - 1 | | Macclesfield |
| Grimsby Town | | 1 - 1 | | Darlington |
| | (2 - 3 pen.) | |
| Hartlepool | | 0 - 0 | | Bristol City |
| | (2 - 4 pen.) | |
| Huddersfield | | 2 - 0 | | Shrewsbury |
| Hull City | | 1 - 1 | | Mansfield Town |
| | (4 - 3 pen.) | |
| Kidderminster | | 2 - 0 | | Scunthorpe United |
| Leyton Orient | | 0 - 0 | | Lincoln City |
| | (2 - 3 pen.) | |
| Luton Town | | 1 - 1 | | Rotherham |
| | (0 - 3 pen.) | |
| Milton Keynes | | 3 - 1 | | Stoke City |
| Northampton | | 0 - 0 | | Doncaster |
| | (4 - 5 pen.) | |
| Peterborough | | 3 - 1 | | Oxford United |
| Rushden | | 0 - 0 | | Derby County |
| | (3 - 0 pen.) | |
| Southend United | | 0 - 2 | | Swindon Town |
| Watford | | 1 - 2 | | Notts County |
| Wrexham | | 1 - 1 | | Barnsley |
| | (3 - 4 pen.) | |
| Yeovil | | 1 - 0 | | Walsall |
| | | | | |
| 15 Sep 2009: Round 2
|
| Arsenal | | 5 - 2 | | Nottm Forest |
| Barnsley | | 0 - 2 | | Chelsea |
| Blackpool | | 1 - 1 | | Wigan Athletic |
| | (0 - 3 pen.) | |
| Bournemouth | | 0 - 3 | | Blackburn |
| Bradford City | | 2 - 2 | | Birmingham |
| | (4 - 2 pen.) | |
| Brighton | | 1 - 1 | | Port Vale |
| | (2 - 4 pen.) | |
| Bristol City | | 0 - 0 | | Reading |
| | (3 - 0 pen.) | |
| Bristol Rovers | | 1 - 2 | | Fulham |
| Burnley | | 1 - 0 | | Leeds United |
| Cheltenham Town | | 0 - 0 | | Norwich |
| | (3 - 4 pen.) | |
| Chesterfield | | 2 - 1 | | Aston Villa |
| Chester | | 1 - 0 | | Wolverhampton |
| Coventry City | | 3 - 1 | | Bolton |
| Crewe | | 2 - 0 | | Everton |
| Crystal Palace | | 3 - 0 | | Ipswich Town |
| Darlington | | 0 - 0 | | Millwall |
| | (4 - 5 pen.) | |
| Doncaster | | 0 - 0 | | Middlesbrough |
| | (4 - 2 pen.) | |
| Gillingham | | 0 - 3 | | Charlton |
| Huddersfield | | 0 - 1 | | Portsmouth |
| Hull City | | 0 - 4 | | Sheffield United |
| Kidderminster | | 0 - 1 | | Cardiff City |
| Lincoln City | | 0 - 1 | | Southampton |
| Manchester City | | 1 - 0 | | QPR |
| Milton Keynes | | 0 - 1 | | Plymouth Argyle |
| Newcastle | | 1 - 1 | | West Ham |
| | (2 - 3 pen.) | |
| Notts County | | 1 - 1 | | Preston |
| | (3 - 0 pen.) | |
| Oldham Athletic | | 0 - 3 | | Sunderland |
| Peterborough | | 0 - 3 | | Liverpool |
| Rotherham | | 1 - 0 | | West Bromwich |
| Rushden | | 0 - 2 | | Leicester City |
| Swindon Town | | 0 - 4 | | Tottenham |
| Yeovil | | 1 - 3 | | Manchester Utd |
| | | | | |
| 13 Oct 2009: Round 3
|
| Arsenal | | 2 - 3 | | Crystal Palace |
| Burnley | | 0 - 2 | | Crewe |
| Cardiff City | | 0 - 3 | | Southampton |
| Charlton | | 3 - 2 | | Fulham |
| Chelsea | | 0 - 2 | | Sheffield United |
| Chester | | 0 - 1 | | Port Vale |
| Coventry City | | 2 - 2 | | Bristol City |
| | (3 - 2 pen.) | |
| Leicester City | | 2 - 0 | | Chesterfield |
| Liverpool | | 2 - 0 | | Bradford City |
| Notts County | | 0 - 1 | | Norwich |
| Plymouth Argyle | | 2 - 0 | | Doncaster |
| Portsmouth | | 2 - 1 | | Blackburn |
| Sunderland | | 0 - 0 | | Rotherham |
| | (2 - 4 pen.) | |
| Tottenham | | 2 - 0 | | Millwall |
| West Ham | | 0 - 2 | | Manchester City |
| Wigan Athletic | | 1 - 5 | | Manchester Utd |
| | | | | |
| 3 Nov 2009: Round 4
|
| Coventry City | | 1 - 2 | | Liverpool |
| Crystal Palace | | 3 - 0 | | Manchester City |
| Manchester Utd | | 4 - 2 | | Tottenham |
| Norwich | | 0 - 3 | | Leicester City |
| Port Vale | | 1 - 2 | | Charlton |
| Rotherham | | 0 - 1 | | Portsmouth |
| Sheffield United | | 1 - 3 | | Crewe |
| Southampton | | 1 - 2 | | Plymouth Argyle |
| | | | | |
| 22 Dec 2009: Quarter-Final
|
| Charlton | | 1 - 3 | | Crystal Palace |
| Leicester City | | 1 - 2 | | Crewe |
| Manchester Utd | | 4 - 3 | | Plymouth Argyle |
| Portsmouth | | 1 - 3 | | Liverpool |
| | | | | |
| 12 Jan 2010: Semi-Final, Leg 1
|
| Crewe | | 1 - 1 | | Liverpool |
| Manchester Utd | | 2 - 1 | | Crystal Palace |
| | | | | |
| 19 Jan 2010: Semi-Final, Leg 2
|
| Crystal Palace | | 5 - 0 | | Manchester Utd |
| | (6 - 2 agg.) | |
| Liverpool | | 5 - 0 | | Crewe |
| | (6 - 1 agg.) | |
| | | | | |
| 31 Jan 2010: Final
|
| Liverpool | | 2 - 3 | | Crystal Palace |