30th May 2009
| Final | Chelsea | 2-1 | Everton |
19th April 2009
| Semi Final | Manchester United | 0-0 | Everton |
18th April 2009
| Semi Final | Arsenal | 1-2 | Chelsea |
17th March 2009
| 6th Round | Arsenal | 2-1 | Hull City |
8th March 2009
| 5th Round | Arsenal | 3-0 | Burnley |
| 6th Round | Everton | 2-1 | Middlesbrough |
7th March 2009
| 6th Round | Coventry City | 0-2 | Chelsea |
| 6th Round | Fulham | 0-4 | Manchester United |
26th February 2009
| 5th Round Replay | Hull City | 2-1 | Sheffield United |
25th February 2009
| 5th Round Replay | Middlesbrough | 2-0 | West Ham United |
24th February 2009
| 5th Round Replay | Coventry City | 1-0 | Blackburn Rovers |
| 5th Round Replay | Fulham | 2-1 | Swansea City |
16th February 2009
| 4th Round Replay | Arsenal | 4-0 | Cardiff City |
15th February 2009
| 5th Round | Derby County | 1-4 | Manchester United |
| 5th Round | Everton | 3-1 | Aston Villa |
14th February 2009
| 5th Round | Blackburn Rovers | 2-2 | Coventry City |
| 5th Round | Sheffield United | 1-1 | Hull City |
| 5th Round | Swansea City | 1-1 | Fulham |
| 5th Round | Watford | 1-3 | Chelsea |
| 5th Round | West Ham United | 1-1 | Middlesbrough |
4th February 2009
| 4th Round Replay | Aston Villa | 3-1 | Doncaster Rovers |
| 4th Round Replay | Blackburn Rovers | 2-1 | Sunderland |
| 4th Round Replay | Everton | 1-0 | Liverpool |
| 4th Round Replay | Nottingham Forest | 2-3 | Derby County |
3rd February 2009
| 4th Round Replay | Burnley | 3-1 | West Bromwich Albion |
25th January 2009
| 4th Round | Cardiff City | 0-0 | Arsenal |
| 4th Round | Liverpool | 1-1 | Everton |
24th January 2009
| 4th Round | Chelsea | 3-1 | Ipswich Town |
| 4th Round | Doncaster Rovers | 0-0 | Aston Villa |
| 4th Round | 0-2 | West Ham United |
| 4th Round | Hull City | 2-0 | Millwall |
| 4th Round | 2-4 | Fulham |
| 4th Round | Manchester United | 2-1 | Tottenham Hotspur |
| 4th Round | Portsmouth | 0-2 | Swansea City |
| 4th Round | Sheffield United | 2-1 | Charlton Athletic |
| 4th Round | Sunderland | 0-0 | Blackburn Rovers |
| 4th Round | 0-1 | Coventry City |
| 4th Round | Watford | 4-3 | Crystal Palace |
| 4th Round | West Bromwich Albion | 2-2 | Burnley |
| 4th Round | Wolverhampton Wanderers | 1-2 | Middlesbrough |
23rd January 2009
| 4th Round | Derby County | 1-1 | Nottingham Forest |
20th January 2009
| 3rd Round Replay | Doncaster Rovers | 3-0 | Cheltenham Town |
14th January 2009
| 3rd Round Replay | Crystal Palace | 2-1 | Leicester City |
| 3rd Round Replay | Newcastle United | 0-1 | Hull City |
| 3rd Round Replay | 1-4 | Chelsea |
13th January 2009
| 3rd Round | Birmingham City | 0-2 | Wolverhampton Wanderers |
| 3rd Round Replay | Bristol City | 0-2 | Portsmouth |
| 3rd Round Replay | Burnley | 2-1 | Queens Park Rangers |
| 3rd Round | Cheltenham Town | 0-0 | Doncaster Rovers |
| 3rd Round Replay | Crewe Alexandra | 2-3 | Millwall |
| 3rd Round | Leyton Orient | 1-4 | Sheffield United |
| 3rd Round Replay | Norwich City | 0-1 | Charlton Athletic |
| 3rd Round Replay | Peterborough United | 0-2 | West Bromwich Albion |
| 3rd Round | 1-2 | Swansea City |
5th January 2009
| 3rd Round | 0-1 | Blackburn Rovers |
4th January 2009
| 3rd Round | Gillingham | 1-2 | Aston Villa |
| 3rd Round | Southampton | 0-3 | Manchester United |
3rd January 2009
| 3rd Round | Arsenal | 3-1 | Plymouth Argyle |
| 3rd Round | Cardiff City | 2-0 | Reading |
| 3rd Round | Charlton Athletic | 1-1 | Norwich City |
| 3rd Round | Chelsea | 1-1 |
| 3rd Round | Coventry City | 2-0 |
| 3rd Round | 3-4 | Derby County |
| 3rd Round | 2-0 | Stoke City |
| 3rd Round | Hull City | 0-0 | Newcastle United |
| 3rd Round | Ipswich Town | 3-0 | Chesterfield |
| 3rd Round | 2-1 |
| 3rd Round | Leicester City | 0-0 | Crystal Palace |
| 3rd Round | 0-1 | Everton |
| 3rd Round | Manchester City | 0-3 | Nottingham Forest |
| 3rd Round | Middlesbrough | 2-1 | Barrow |
| 3rd Round | Millwall | 2-2 | Crewe Alexandra |
| 3rd Round | Portsmouth | 0-0 | Bristol City |
| 3rd Round | Preston North End | 0-2 | Liverpool |
| 3rd Round | Queens Park Rangers | 0-0 | Burnley |
| 3rd Round | Sheffield Wednesday | 1-2 | Fulham |
| 3rd Round | Sunderland | 2-1 | Bolton Wanderers |
| 3rd Round | 1-0 | Blackpool |
| 3rd Round | Watford | 1-0 |
| 3rd Round | West Bromwich Albion | 1-1 | Peterborough United |
| 3rd Round | West Ham United | 3-0 | Barnsley |
2nd January 2009
| 3rd Round | Tottenham Hotspur | 3-1 | Wigan Athletic |
23rd December 2008
| 2nd Round Replay | 2-1 | Chesterfield |
16th December 2008
| 2nd Round Replay | 1-0 | AFC Bournemouth |
10th December 2008
| 2nd Round Replay | 2-1 | Notts. County |
9th December 2008
| 2nd Round | Chesterfield | 2-2 |
| 2nd Round Replay | Stockport County | 1-2 | Gillingham |
| 2nd Round Replay | Tranmere Rovers | 1-2 | Peterborough United |
3rd December 2008
| 2nd Round | 0-2 | Crewe Alexandra |
2nd December 2008
| 2nd Round | 2-3 | Cheltenham Town |
30th November 2008
| 2nd Round | Notts. County | 1-1 |
| 2nd Round | 1-0 | Leeds United |
29th November 2008
| 2nd Round | AFC Bournemouth | 0-0 |
| 2nd Round | Bradford City | 1-2 | Leyton Orient |
| 2nd Round | 2-0 | Wycombe Wanderers |
| 2nd Round | Fleetwood Town | 2-3 |
| 2nd Round | 2-0 |
| 2nd Round | Gillingham | 0-0 | Stockport County |
| 1st Round Replay | 0-2 |
| 2nd Round | 2-0 |
| 2nd Round | Leicester City | 3-2 |
| 2nd Round | Millwall | 3-0 |
| 2nd Round | Peterborough United | 0-0 | Tranmere Rovers |
| 2nd Round | 4-0 |
| 2nd Round | 3-1 | Luton Town |
| 2nd Round | 2-0 | Oxford United |
28th November 2008
| 2nd Round | Barrow | 2-1 | Brentford |
| 2nd Round | Port Vale | 1-3 |
18th November 2008
| 1st Round Replay | 0-0 | Luton Town |
| 1st Round Replay | Barrow | 4-0 |
| 1st Round Replay | 2-1 |
| 1st Round Replay | 1-3 | Oxford United |
| 1st Round Replay | 1-0 |
| 1st Round Replay | Fleetwood Town | 2-0 |
| 1st Round Replay | 2-1 | Brighton & Hove Albion |
| 1st Round Replay | Lincoln City | 1-2 |
| 1st Round Replay | Oldham Athletic | 0-1 | Cheltenham Town |
| 1st Round Replay | 3-2 | Barnet |
| 1st Round Replay | Rotherham United | 0-3 |
| 1st Round Replay | 2-0 |
| 1st Round Replay | Stockport County | 5-0 |
17th November 2008
| 1st Round Replay | Northampton Town | 2-5 | Leeds United |
13th November 2008
| 1st Round Replay | Tranmere Rovers | 1-0 | Accrington Stanley |
10th November 2008
| 1st Round | AFC Wimbledon | 1-4 | Wycombe Wanderers |
9th November 2008
| 1st Round | 1-3 | Brentford |
| 1st Round | 0-1 | Peterborough United |
| 1st Round | 0-1 |
8th November 2008
| 1st Round | Accrington Stanley | 0-0 | Tranmere Rovers |
| 1st Round | 1-1 | Rotherham United |
| 1st Round | 4-2 |
| 1st Round | Barnet | 1-1 |
| 1st Round | 3-1 | Shrewsbury Town |
| 1st Round | AFC Bournemouth | 1-0 | Bristol Rovers |
| 1st Round | Brighton & Hove Albion | 3-3 |
| 1st Round | 0-1 | Gillingham |
| 1st Round | 1-1 |
| 1st Round | Cheltenham Town | 2-2 | Oldham Athletic |
| 1st Round | 0-3 | Millwall |
| 1st Round | Chesterfield | 3-1 | Mansfield Town |
| 1st Round | Colchester United | 0-1 | Leyton Orient |
| 1st Round | Crewe Alexandra | 1-0 |
| 1st Round | 3-2 | Exeter City |
| 1st Round | 0-0 |
| 1st Round | 2-1 |
| 1st Round | 0-2 |
| 1st Round | 0-0 |
| 1st Round | Huddersfield Town | 3-4 | Port Vale |
| 1st Round | 1-1 | Lincoln City |
| 1st Round | 1-0 | Cambridge United |
| 1st Round | Leicester City | 3-0 | Stevenage |
| 1st Round | Luton Town | 0-0 |
| 1st Round | 2-1 | Grimsby Town |
| 1st Round | Oxford United | 0-0 |
| 1st Round | 0-1 | Notts. County |
| 1st Round | 2-2 |
| 1st Round | 2-0 |
| 1st Round | Walsall | 1-3 |
| 1st Round | Milton Keynes Dons | 1-2 | Bradford City |
| 1st Round | 1-1 | Stockport County |
| 1st Round | 1-0 | Swindon Town |
| 1st Round | 0-0 | Barrow |
| 1st Round | 0-0 | Fleetwood Town |
7th November 2008
| 1st Round | Leeds United | 1-1 | Northampton Town |