League Cup competition results from 2008/2009
A full listing of matches played in the competition throughout the season
| 4th Round |
| Tuesday, 11th November 2008 |
| Arsenal (PREM) | 3 | Wigan Athletic (PREM) | 0 | 59,665 |
| Derby County (CHMP) | 2 | Leeds United (LGE1) | 1 | 18,540 |
| Manchester United (PREM) | 1 | Queens Park Rangers (CHMP) | 0 | 62,539 |
| Stoke City (PREM) | 2 | Rotherham United (LGE2) | 0 | 15,458 |
| Swansea City (CHMP) | 0 | Watford (CHMP) | 1 | 9,549 |
| Wednesday, 12th November 2008 |
| Chelsea (PREM) | 1 | Burnley (CHMP) | 1 | 41,369 |
| after extra time, 90 minutes 1-1, Burnley won 5-4 on penalties |
| Sunderland (PREM) | 1 | Blackburn Rovers (PREM) | 2 | 18,555 |
| Tottenham Hotspur (PREM) | 4 | Liverpool (PREM) | 2 | 33,242 |
| 3rd Round |
| Tuesday, 23rd September 2008 |
| Arsenal (PREM) | 6 | Sheffield United (CHMP) | 0 | 56,632 |
| Burnley (CHMP) | 1 | Fulham (PREM) | 0 | 7,119 |
| Leeds United (LGE1) | 3 | Hartlepool United (LGE1) | 2 | 14,599 |
| Liverpool (PREM) | 2 | Crewe Alexandra (LGE1) | 1 | 28,591 |
| Manchester United (PREM) | 3 | Middlesbrough (PREM) | 1 | 53,729 |
| Rotherham United (LGE2) | 3 | Southampton (CHMP) | 1 | 5,147 |
| Stoke City (PREM) | 2 | Reading (CHMP) | 2 | 9,141 |
| after extra time, 90 minutes 2-2, Stoke City won 4-3 on penalties |
| Sunderland (PREM) | 2 | Northampton Town (LGE1) | 2 | 21,082 |
| after extra time, 90 minutes 2-2, Sunderland won 4-3 on penalties |
| Swansea City (CHMP) | 1 | Cardiff City (CHMP) | 0 | 17,411 |
| Watford (CHMP) | 1 | West Ham United (PREM) | 0 | 12,914 |
| Wednesday, 24th September 2008 |
| Aston Villa (PREM) | 0 | Queens Park Rangers (CHMP) | 1 | 21,541 |
| Blackburn Rovers (PREM) | 1 | Everton (PREM) | 0 | 14,366 |
| Ipswich Town (CHMP) | 1 | Wigan Athletic (PREM) | 4 | 13,803 |
| Newcastle United (PREM) | 1 | Tottenham Hotspur (PREM) | 2 | 20,577 |
| Portsmouth (PREM) | 0 | Chelsea (PREM) | 4 | 15,339 |
| Tuesday, 4th November 2008 |
| Brighton & Hove Albion (LGE1) | 1 | Derby County (CHMP) | 4 | 6,625 |
| 2nd Round |
| Tuesday, 26th August 2008 |
| Bolton Wanderers (PREM) | 1 | Northampton Town (LGE1) | 2 | 7,136 |
| Burnley (CHMP) | 3 | Oldham Athletic (LGE1) | 0 | 5,528 |
| Cardiff City (CHMP) | 2 | Milton Keynes Dons (LGE1) | 1 | 6,334 |
| Cheltenham Town (LGE1) | 2 | Stoke City (PREM) | 3 | 3,600 |
| Coventry City (CHMP) | 2 | Newcastle United (PREM) | 3 | 19,249 |
| after extra time, 90 minutes 2-2 |
| Crewe Alexandra (LGE1) | 2 | Bristol City (CHMP) | 1 | 3,227 |
| Hartlepool United (LGE1) | 3 | West Bromwich Albion (PREM) | 1 | 3,387 |
| after extra time, 90 minutes 1-1 |
| Ipswich Town (CHMP) | 2 | Colchester United (LGE1) | 1 | 17,084 |
| Leeds United (LGE1) | 4 | Crystal Palace (CHMP) | 0 | 10,765 |
| Middlesbrough (PREM) | 5 | Yeovil Town (LGE1) | 1 | 15,651 |
| Preston North End (CHMP) | 0 | Derby County (CHMP) | 1 | 8,037 |
| Queens Park Rangers (CHMP) | 4 | Carlisle United (LGE1) | 0 | 8,021 |
| Reading (CHMP) | 5 | Luton Town (LGE2) | 1 | 7,498 |
| Rotherham United (LGE2) | 0 | Wolverhampton Wanderers (CHMP) | 0 | 5,404 |
| after extra time, Rotherham United won 4-3 on penalties |
| Southampton (CHMP) | 2 | Birmingham City (CHMP) | 0 | 11,331 |
| Swansea City (CHMP) | 2 | Hull City (PREM) | 1 | 8,622 |
| after extra time, 90 minutes 1-1 |
| Watford (CHMP) | 2 | Darlington (LGE2) | 1 | 5,236 |
| after extra time, 90 minutes 1-1 |
| Wigan Athletic (PREM) | 4 | Notts. County (LGE2) | 0 | 4,100 |
| Wednesday, 27th August 2008 |
| Blackburn Rovers (PREM) | 4 | Grimsby Town (LGE2) | 1 | 8,379 |
| Fulham (PREM) | 3 | Leicester City (LGE1) | 2 | 7,584 |
| Huddersfield Town (LGE1) | 1 | Sheffield United (CHMP) | 2 | 15,189 |
| Nottingham Forest (CHMP) | 1 | Sunderland (PREM) | 2 | 9,198 |
| after extra time, 90 minutes 1-1 |
| West Ham United (PREM) | 4 | Macclesfield Town (LGE2) | 1 | 10,055 |
| after extra time, 90 minutes 1-1 |
| Wednesday, 24th September 2008 |
| Brighton & Hove Albion (LGE1) | 2 | Manchester City (PREM) | 2 | 8,729 |
| after extra time, 90 minutes 1-1, Brighton & Hove Albion won 5-3 on penalties |
| 1st Round |
| Tuesday, 12th August 2008 |
| Bournemouth (LGE2) | 1 | Cardiff City (CHMP) | 2 | 3,399 |
| Brighton & Hove Albion (LGE1) | 4 | Barnet (LGE2) | 0 | 2,571 |
| Bristol City (CHMP) | 2 | Peterborough United (LGE1) | 1 | 5,684 |
| Bury (LGE2) | 0 | Burnley (CHMP) | 2 | 4,276 |
| Charlton Athletic (CHMP) | 0 | Yeovil Town (LGE1) | 1 | 6,239 |
| Chester City (LGE2) | 2 | Leeds United (LGE1) | 5 | 3,644 |
| Crewe Alexandra (LGE1) | 2 | Barnsley (CHMP) | 0 | 2,492 |
| Crystal Palace (CHMP) | 2 | Hereford United (LGE1) | 1 | 3,094 |
| Dagenham & Redbridge (LGE2) | 1 | Reading (CHMP) | 2 | 2,360 |
| Derby County (CHMP) | 3 | Lincoln City (LGE2) | 1 | 10,091 |
| after extra time, 90 minutes 1-1 |
| Exeter City (LGE2) | 1 | Southampton (CHMP) | 3 | 6,471 |
| Gillingham (LGE2) | 0 | Colchester United (LGE1) | 1 | 2,566 |
| Grimsby Town (LGE2) | 2 | Tranmere Rovers (LGE1) | 0 | 1,858 |
| Hartlepool United (LGE1) | 3 | Scunthorpe United (LGE1) | 0 | 2,076 |
| Huddersfield Town (LGE1) | 4 | Bradford City (LGE2) | 0 | 8,932 |
| Ipswich Town (CHMP) | 4 | Leyton Orient (LGE1) | 1 | 10,477 |
| Leicester City (LGE1) | 1 | Stockport County (LGE1) | 0 | 7,386 |
| Luton Town (LGE2) | 2 | Plymouth Argyle (CHMP) | 0 | 2,682 |
| Macclesfield Town (LGE2) | 2 | Blackpool (CHMP) | 0 | 1,631 |
| Millwall (LGE1) | 0 | Northampton Town (LGE1) | 1 | 3,525 |
| Milton Keynes Dons (LGE1) | 1 | Norwich City (CHMP) | 0 | 6,261 |
| Notts. County (LGE2) | 1 | Doncaster Rovers (CHMP) | 0 | 3,272 |
| after extra time, 90 minutes 0-0 |
| Preston North End (CHMP) | 2 | Chesterfield (LGE2) | 0 | 5,150 |
| Rochdale (LGE2) | 0 | Oldham Athletic (LGE1) | 0 | 5,786 |
| after extra time, 90 minutes 0-0, Oldham Athletic won 4-1 on penalties |
| Sheffield Wednesday (CHMP) | 2 | Rotherham United (LGE2) | 2 | 16,298 |
| after extra time, 90 minutes 1-1, Rotherham United won 5-3 on penalties |
| Shrewsbury Town (LGE2) | 0 | Carlisle United (LGE1) | 1 | 3,337 |
| Southend United (LGE1) | 0 | Cheltenham Town (LGE1) | 1 | 2,998 |
| after extra time |
| Swansea City (CHMP) | 2 | Brentford (LGE2) | 0 | 5,366 |
| Swindon Town (LGE1) | 2 | Queens Park Rangers (CHMP) | 3 | 7,230 |
| Walsall (LGE1) | 1 | Darlington (LGE2) | 2 | 2,702 |
| Watford (CHMP) | 1 | Bristol Rovers (LGE1) | 0 | 5,574 |
| Wolverhampton Wanderers (CHMP) | 3 | Accrington Stanley (LGE2) | 2 | 9,424 |
| after extra time, 90 minutes 1-1 |
| Wednesday, 13th August 2008 |
| Coventry City (CHMP) | 3 | Aldershot Town (LGE2) | 1 | 9,293 |
| Nottingham Forest (CHMP) | 4 | Morecambe (LGE2) | 0 | 4,030 |
| Sheffield United (CHMP) | 3 | Port Vale (LGE2) | 1 | 7,694 |
| Wycombe Wanderers (LGE2) | 0 | Birmingham City (CHMP) | 4 | 2,735 |
