| Monday 24th August 2009 | |||
| Norwich City | 1-4 | Sunderland | |
| Tuesday 25th August 2009 | |||
| Gillingham | 1-3 | Blackburn Rovers | |
| Hartlepool United | 1-2 | Burnley | aet |
| Hull City | 3-1 | Southend United | |
| Leeds United | 2-1 | Watford | aet |
| Nottingham Forest | 2-1 | Middlesbrough | aet |
| Peterborough United | 2-1 | Ipswich Town | |
| Port Vale | 2-0 | Sheffield Wednesday | |
| Portsmouth | 4-1 | Hereford United | |
| Preston North End | 2-1 | Leicester City | |
| Queens Park Rangers | 2-1 | Accrington Stanley | |
| Reading | 1-2 | Barnsley | |
| Southampton | 1-2 | Birmingham City | |
| Swansea City | 1-2 | Scunthorpe United | aet |
| Tranmere Rovers | 0-1 | Bolton Wanderers | |
| West Ham United | 3-1 | Millwall | aet |
| Wolverhampton Wndrs | 0-0 | Swindon Town | aet |
| (Wolverhampton Wndrs won on penalties) | |||
| Wednesday 26th August 2009 | |||
| Blackpool | 4-1 | Wigan Athletic | |
| Bristol City | 0-2 | Carlisle United | |
| Cardiff City | 3-1 | Bristol Rovers | |
| Doncaster Rovers | 1-5 | Tottenham Hotspur | |
| Leyton Orient | 0-1 | Stoke City | aet |
| Newcastle United | 4-3 | Huddersfield Town | |
| West Bromwich Albion | 4-3 | Rotherham United | aet |
| Thursday 27th August 2009 | |||
| Crystal Palace | 0-2 | Manchester City | |
