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