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