| Accrington Stanley | 2 – 1 | Walsall | 1,041 |
| Huddersfield Town | 3 – 1 | Stockport County | 5,120 |
| Rotherham United | 2 – 1 | Derby County | 4,345 |
| Tranmere Rovers | 4 – 0 | Grimsby Town | 3,527 |
| Sheffield Wednesday | 3 – 0 | Rochdale | 6,696 |
| Bury | 0 – 2 | West Bromwich Albion | 3,077 |
| Notts County | 0 – 1 | Doncaster Rovers | 4,893 |
| Lincoln City | 0 – 1 | Barnsley | 3,635 |
| Scunthorpe United | 2 – 1 | Chesterfield | 2,501 |
| Coventry City | 0 – 0 | Hartlepool United | 6,055 |
| Hartlepool United won 1 – 0 after extra time | | | |
| Darlington | 0 – 1 | Leeds United | 4,487 |
| Preston North End | 5 – 1 | Morecambe | 5,407 |
| Crewe Alexandra | 1 – 2 | Blackpool | 2,991 |
| Carlisle United | 1 – 0 | Oldham Athletic | 2,509 |
| Nottingham Forest | 3 – 0 | Bradford City | 4,639 |
| Macclesfield Town | 0 – 2 | Leicester City | 2,197 |
| Sheffield United | 1 – 2 | Port Vale | 7,627 |
| | | |
| CARLING CUP FIRST ROUND (SOUTH) | | | |
| Cardiff City | 3 – 1 | Dagenham & Redbridge | 5,545 |
| Wycombe Wanderers | 0 – 4 | Peterborough United | 2,078 |
| Southampton | 2 – 0 | Northampton Town | 10,921 |
| Barnet | 0 – 0 | Watford | 3,139 |
| Watford won 2 – 0 after extra time | | | |
| Hereford United | 0 – 0 | Charlton Athletic | 2,017 |
| Hereford United won 1 – 0 after extra time | | | |
| Bristol Rovers | 2 – 1 | Aldershot Town | 3,644 |
| Millwall | 4 – 0 | AFC Bournemouth | 3,552 |
| Gillingham | 2 – 1 | Plymouth Argyle | 3,306 |
| Colchester United | 1 – 2 | Leyton Orient | 3,308 |
| Reading | 5 – 1 | Burton Albion | 5,893 |
| Exeter City | 0 – 5 | Queens Park Rangers | 4,614 |
| Cheltenham Town | 1 – 2 | Southend United | 1,918 |
| Brentford | 0 – 1 | Bristol City | 3,024 |
| Yeovil Town | 0 – 4 | Norwich City | 3,860 |
| Crystal Palace | 2 – 1 | Torquay United | 3,140 |
| Milton Keynes Dons | 1 – 4 | Swindon Town | 4,812 |
| Swansea City | 3 – 0 | Brighton & Hove Albion | 6,400 |
| Shrewsbury Town | 3 – 3 | Ipswich Town | 4,184 |
| 3 – 3 after extra time – Ipswich Town won 4 – 2 on penalties | | | |
| | | |
| CARLING CUP SECOND ROUND | | | |
| West Bromwich Albion | 2 – 2 | Rotherham United | 10,659 |
| West Bromwich Albion won 4 – 3 after extra time | | | |
| Norwich City | 1 – 4 | Sunderland | 12,345 |
| Tranmere Rovers | 0 – 1 | Bolton Wanderers | 5,381 |
| Queens Park Rangers | 2 – 1 | Accrington Stanley | 5,203 |
| Bristol City | 0 – 2 | Carlisle United | 6,359 |
| Leyton Orient | 0 – 0 | Stoke City | 2,742 |
| Stoke City won 1 – 0 after extra time | | | |
| Port Vale | 2 – 0 | Sheffield Wednesday | 6,667 |
| Hull City | 3 – 1 | Southend United | 7,994 |
| Leeds United | 1 – 1 | Watford | 14,681 |
| Leeds United won 2 – 1 after extra time | | | |
| Cardiff City | 3 – 1 | Bristol Rovers | 9,767 |
| Portsmouth | 4 – 1 | Hereford United | 6,645 |
| Crystal Palace | 0 – 2 | Manchester City | 14,725 |
| Wolverhampton Wand | 0 – 0 | Swindon Town | 11,416 |
| 0 – 0 aet Wolverhampton Wand won 6 – 5 on penalties | | | |
| Gillingham | 1 – 3 | Blackburn Rovers | 7,203 |
| Blackpool | 4 – 1 | Wigan Athletic | 8,089 |
| Southampton | 1 – 2 | Birmingham City | 11,753 |
| Preston North End | 2 – 1 | Leicester City | 6,977 |
| Newcastle United | 4 – 3 | Huddersfield Town | 23,815 |
| West Ham United | 1 – 1 | Millwall | 24,492 |
| West Ham United won 3 – 1 after extra time | | | |
| Hartlepool United | 1 – 1 | Burnley | 3,501 |
| Burnley won 2 – 1 after extra time | | | |
| Nottingham Forest | 1 – 1 | Middlesbrough | 8,838 |
| Nottingham Forest won 2 – 1 after extra time | | | |
| Reading | 1 – 2 | Barnsley | 5,576 |
| Swansea City | 1 – 2 | Scunthorpe United | 7,321 |
| Doncaster Rovers | 1 – 5 | Tottenham Hotspur | 12,923 |
| Peterborough United | 2 – 1 | Ipswich Town | 5,451 |
| | | |
| CARLING CUP THIRD ROUND | | | |
| Arsenal | 2 – 0 | West Bromwich Albion | 56,592 |
| Chelsea | 1 – 0 | Queens Park Rangers | 37,781 |
| Bolton Wanderers | 1 – 1 | West Ham United | 8,050 |
| Bolton Wanderers won 3 – 1 after extra time | | | |
| Barnsley | 3 – 2 | Burnley | 6,270 |
| Hull City | 0 – 4 | Everton | 13,558 |
| Leeds United | 0 – 1 | Liverpool | 38,168 |
| Manchester United | 1 – 0 | Wolverhampton Wand | 51,160 |
| Manchester City | 1 – 1 | Fulham | 24,507 |
| Manchester City won 2 – 1 after extra time | | | |
| Sunderland | 2 – 0 | Birmingham City | 20,576 |
| Peterborough United | 2 – 0 | Newcastle United | 10,298 |
| Carlisle United | 1 – 3 | Portsmouth | 7,042 |
| Nottingham Forest | 0 – 1 | Blackburn Rovers | 11,553 |
| Stoke City | 4 – 3 | Blackpool | 13,957 |
| Scunthorpe United | 0 – 0 | Port Vale | 3,383 |
| Scunthorpe United won 2 – 0 after extra time | | | |
| Preston North End | 1 – 5 | Tottenham Hotspur | 16,533 |
| Aston Villa | 1 – 0 | Cardiff City | 22,527 |
| | | |
| CARLING CUP FOURTH ROUND | | | |
| Blackburn Rovers | 5 – 2 | Peterborough United | 8,419 |
| Portsmouth | 4 – 0 | Stoke City | 11,251 |
| Tottenham Hotspur | 2 – 0 | Everton | 35,843 |
| Barnsley | 0 – 2 | Manchester United | 20,019 |
| Sunderland | 0 – 0 | Aston Villa | 27,666 |
| 0 – 0 aet Aston Villa won 3 – 1 on penalties | | | |
| Arsenal | 2 – 1 | Liverpool | 60,004 |
| Chelsea | 4 – 0 | Bolton Wanderers | 41,538 |
| Manchester City | 5 – 1 | Scunthorpe United | 36,358 |
| | | |
| CARLING CUP FIFTH ROUND (QUARTER FINALS) | | | |
| Manchester United | 2 – 0 | Tottenham Hotspur | 57,212 |
| Portsmouth | 2 – 4 | Aston Villa | 17,034 |
| Blackburn Rovers | 2 – 2 | Chelsea | 18,136 |
| 3 – 3 aet Blackburn won 4 – 3 on penalties | | | |
| Manchester City | 3 – 0 | Arsenal | 46,015 |
| | | |
| CARLING CUP SEMI-FINALS (Two Legs) | | | |
| Blackburn Rovers | 0 – 1 | Aston Villa | 18,595 |
| Aston Villa | 6 – 4 | Blackburn Rovers | 40,406 |
| Manchester City | 2 – 1 | Manchester United | 46,067 |
| Manchester United | 3 – 1 | Manchester City | 74,576 |
| | | |
| CARLING CUP FINAL (Wembley Sun 28th Feb 2010) | | | |
| Manchester United | 2 – 1 | Aston Villa | 88,596 |
