First Round | ||||||
|---|---|---|---|---|---|---|
| 07 Nov 2008 | Leeds United | 1:1 | Northampton Town | |||
| 08 Nov 2008 | Accrington Stanley | 0:0 | Tranmere Rovers | |||
| 08 Nov 2008 | AFC Bournemouth | 1:0 | Bristol Rovers | |||
| 08 Nov 2008 | AFC Telford United | 2:2 | Southend United | |||
| 08 Nov 2008 | Aldershot Town | 1:1 | Rotherham United | |||
| 08 Nov 2008 | Alfreton Town | 4:2 | Bury Town | |||
| 08 Nov 2008 | Barnet | 1:1 | Rochdale | |||
| 08 Nov 2008 | Blyth Spartans | 3:1 | Shrewsbury Town | |||
| 08 Nov 2008 | Brighton and Hove Albion | 3:3 | Hartlepool United | |||
| 08 Nov 2008 | Bury | 0:1 | Gillingham | |||
| 08 Nov 2008 | Carlisle United | 1:1 | Grays Athletic | |||
| 08 Nov 2008 | Cheltenham Town | 2:2 | Oldham Athletic | |||
| 08 Nov 2008 | Chester City | 0:3 | Millwall | |||
| 08 Nov 2008 | Chesterfield | 3:1 | Mansfield Town | |||
| 08 Nov 2008 | Colchester United | 0:1 | Leyton Orient | |||
| 08 Nov 2008 | Crewe Alexandra | 1:0 | Ebbsfleet United | |||
| 08 Nov 2008 | Curzon Ashton | 3:2 | Exeter City | |||
| 08 Nov 2008 | Darlington | 0:0 | Droylsden | |||
| 08 Nov 2008 | Eastbourne Borough | 0:0 | Barrow | |||
| 08 Nov 2008 | Eastwood Town | 2:1 | Brackley Town | |||
| 08 Nov 2008 | Harlow Town | 0:2 | Macclesfield Town | |||
| 08 Nov 2008 | Hereford United | 0:0 | Dagenham and Redbridge | |||
| 08 Nov 2008 | Histon | 1:0 | Swindon Town | |||
| 08 Nov 2008 | Huddersfield Town | 3:4 | Port Vale | |||
| 08 Nov 2008 | Kettering Town | 1:1 | Lincoln City | |||
| 08 Nov 2008 | Kidderminster Harriers | 1:0 | Cambridge United | |||
| 08 Nov 2008 | Leicester City | 3:0 | Stevenage Borough | |||
| 08 Nov 2008 | Leiston | 0:0 | Fleetwood Town | |||
| 08 Nov 2008 | Luton Town | 0:0 | Altrincham | |||
| 08 Nov 2008 | Milton Keynes Dons | 1:2 | Bradford City | |||
| 08 Nov 2008 | Morecambe | 2:1 | Grimsby Town | |||
| 08 Nov 2008 | Oxford United | 0:0 | Dorchester Town | |||
| 08 Nov 2008 | Sutton United | 0:1 | Notts County | |||
| 08 Nov 2008 | Torquay United | 2:0 | Evesham United | |||
| 08 Nov 2008 | Walsall | 1:3 | Scunthorpe United | |||
| 08 Nov 2008 | Yeovil Town | 1:1 | Stockport County | |||
| 09 Nov 2008 | AFC Hornchurch | 0:1 | Peterborough United | |||
| 09 Nov 2008 | Havant and Waterlooville | 1:3 | Brentford | |||
| 09 Nov 2008 | Team Bath | 0:1 | Forest Green Rovers | |||
| 10 Nov 2008 | AFC Wimbledon | 1:4 | Wycombe Wanderers | |||
| 13 Nov 2008 | Tranmere Rovers | 1:0 | Accrington Stanley | replay | ||
| 17 Nov 2008 | Northampton Town | 2:5 | Leeds United | replay | ||
| 18 Nov 2008 | Altrincham | 0:0 (2:4) | Luton Town | replay | ||
| 18 Nov 2008 | Barrow | 4:0 | Eastbourne Borough | replay | ||
| 18 Nov 2008 | Dagenham and Redbridge | 2:1 | Hereford United | replay | ||
| 18 Nov 2008 | Dorchester Town | 1:3 | Oxford United | replay | ||
| 18 Nov 2008 | Droylsden | 1:0 | Darlington | replay | ||
| 18 Nov 2008 | Fleetwood Town | 2:0 | Leiston | replay | ||
| 18 Nov 2008 | Hartlepool United | 2:1 | Brighton and Hove Albion | replay | ||
| 18 Nov 2008 | Lincoln City | 1:2 | Kettering Town | replay | ||
| 18 Nov 2008 | Oldham Athletic | 0:1 | Cheltenham Town | replay | ||
| 18 Nov 2008 | Rochdale | 3:2 | Barnet | replay | ||
| 18 Nov 2008 | Rotherham United | 0:3 | Aldershot Town | replay | ||
| 18 Nov 2008 | Southend United | 2:0 | AFC Telford United | replay | ||
| 18 Nov 2008 | Stockport County | 5:0 | Yeovil Town | replay | ||
| 29 Nov 2008 | Grays Athletic | 0:2 | Carlisle United | replay | ||
Second Round | ||||||
| 28 Nov 2008 | Barrow | 2:1 | Brentford | |||
| 28 Nov 2008 | Port Vale | 1:3 | Macclesfield Town | |||
| 29 Nov 2008 | AFC Bournemouth | 0:0 | Blyth Spartans | |||
| 29 Nov 2008 | Bradford City | 1:2 | Leyton Orient | |||
| 29 Nov 2008 | Eastwood Town | 2:0 | Wycombe Wanderers | |||
| 29 Nov 2008 | Fleetwood Town | 2:3 | Hartlepool United | |||
| 29 Nov 2008 | Forest Green Rovers | 2:0 | Rochdale | |||
| 29 Nov 2008 | Gillingham | 0:0 | Stockport County | |||
| 29 Nov 2008 | Kidderminster Harriers | 2:0 | Curzon Ashton | |||
| 29 Nov 2008 | Leicester City | 3:2 | Dagenham and Redbridge | |||
| 29 Nov 2008 | Millwall | 3:0 | Aldershot Town | |||
| 29 Nov 2008 | Peterborough United | 0:0 | Tranmere Rovers | |||
| 29 Nov 2008 | Scunthorpe United | 4:0 | Alfreton Town | |||
| 29 Nov 2008 | Southend United | 3:1 | Luton Town | |||
| 29 Nov 2008 | Torquay United | 2:0 | Oxford United | |||
| 30 Nov 2008 | Histon | 1:0 | Leeds United | |||
| 30 Nov 2008 | Notts County | 1:1 | Kettering Town | |||
| 02 Dec 2008 | Morecambe | 2:3 | Cheltenham Town | |||
| 03 Dec 2008 | Carlisle United | 0:2 | Crewe Alexandra | |||
| 09 Dec 2008 | Chesterfield | 2:2 | Droylsden | |||
| 09 Dec 2008 | Stockport County | 1:2 | Gillingham | replay | ||
| 09 Dec 2008 | Tranmere Rovers | 1:2 | Peterborough United | replay | ||
| 10 Dec 2008 | Kettering Town | 2:1 | Notts County | replay | ||
| 16 Dec 2008 | Blyth Spartans | 1:0 | AFC Bournemouth | replay | ||
| 23 Dec 2008 | Droylsden | 2:1 | Chesterfield | replay | ||
Third Round | ||||||
| 02 Jan 2009 | Tottenham Hotspur | 3:1 | Wigan Athletic | |||
| 03 Jan 2009 | Arsenal | 3:1 | Plymouth Argyle | |||
| 03 Jan 2009 | Cardiff City | 2:0 | Reading | |||
| 03 Jan 2009 | Charlton Athletic | 1:1 | Norwich City | |||
| 03 Jan 2009 | Chelsea | 1:1 | Southend United | |||
| 03 Jan 2009 | Coventry City | 2:0 | Kidderminster Harriers | |||
| 03 Jan 2009 | Forest Green Rovers | 3:4 | Derby County | |||
| 03 Jan 2009 | Hartlepool United | 2:0 | Stoke City | |||
| 03 Jan 2009 | Hull City | 0:0 | Newcastle United | |||
| 03 Jan 2009 | Ipswich Town | 3:0 | Chesterfield | |||
| 03 Jan 2009 | Kettering Town | 2:1 | Eastwood Town | |||
| 03 Jan 2009 | Leicester City | 0:0 | Crystal Palace | |||
| 03 Jan 2009 | Macclesfield Town | 0:1 | Everton | |||
| 03 Jan 2009 | Manchester City | 0:3 | Nottingham Forest | |||
| 03 Jan 2009 | Middlesbrough | 2:1 | Barrow | |||
| 03 Jan 2009 | Millwall | 2:2 | Crewe Alexandra | |||
| 03 Jan 2009 | Portsmouth | 0:0 | Bristol City | |||
| 03 Jan 2009 | Preston North End | 0:2 | Liverpool | |||
| 03 Jan 2009 | Queens Park Rangers | 0:0 | Burnley | |||
| 03 Jan 2009 | Sheffield Wednesday | 1:2 | Fulham | |||
| 03 Jan 2009 | Sunderland | 2:1 | Bolton Wanderers | |||
| 03 Jan 2009 | Torquay United | 1:0 | Blackpool | |||
| 03 Jan 2009 | Watford | 1:0 | Scunthorpe United | |||
| 03 Jan 2009 | West Bromwich Albion | 1:1 | Peterborough United | |||
| 03 Jan 2009 | West Ham United | 3:0 | Barnsley | |||
| 04 Jan 2009 | Gillingham | 1:2 | Aston Villa | |||
| 04 Jan 2009 | Southampton | 0:3 | Manchester United | |||
| 05 Jan 2009 | Blyth Spartans | 0:1 | Blackburn Rovers | |||
| 13 Jan 2009 | Birmingham City | 0:2 | Wolverhampton Wanderers | |||
| 13 Jan 2009 | Cheltenham Town | 0:0 | Doncaster Rovers | |||
| 13 Jan 2009 | Histon | 1:2 | Swansea City | |||
| 13 Jan 2009 | Leyton Orient | 1:4 | Sheffield United | |||
| 13 Jan 2009 | Bristol City | 0:2 | Portsmouth | replay | ||
| 13 Jan 2009 | Burnley | 2:1 | Queens Park Rangers | replay | ||
| 13 Jan 2009 | Crewe Alexandra | 2:3 | Millwall | replay | ||
| 13 Jan 2009 | Norwich City | 0:1 | Charlton Athletic | replay | ||
| 13 Jan 2009 | Peterborough United | 0:2 | West Bromwich Albion | replay | ||
| 14 Jan 2009 | Crystal Palace | 2:1 | Leicester City | replay | ||
| 14 Jan 2009 | Newcastle United | 0:1 | Hull City | replay | ||
| 14 Jan 2009 | Southend United | 1:4 | Chelsea | replay | ||
| 20 Jan 2009 | Doncaster Rovers | 3:0 | Cheltenham Town | replay | ||
Fourth Round | ||||||
| 26 Jan 2008 | Derby County | 1:4 | Preston North End | |||
| 23 Jan 2009 | Derby County | 1:1 | Nottingham Forest | |||
| 24 Jan 2009 | Chelsea | 3:1 | Ipswich Town | |||
| 24 Jan 2009 | Doncaster Rovers | 0:0 | Aston Villa | |||
| 24 Jan 2009 | Hartlepool United | 0:2 | West Ham United | |||
| 24 Jan 2009 | Hull City | 2:0 | Millwall | |||
| 24 Jan 2009 | Kettering Town | 2:4 | Fulham | |||
| 24 Jan 2009 | Manchester United | 2:1 | Tottenham Hotspur | |||
| 24 Jan 2009 | Portsmouth | 0:2 | Swansea City | |||
| 24 Jan 2009 | Sheffield United | 2:1 | Charlton Athletic | |||
| 24 Jan 2009 | Sunderland | 0:0 | Blackburn Rovers | |||
| 24 Jan 2009 | Torquay United | 0:1 | Coventry City | |||
| 24 Jan 2009 | Watford | 4:3 | Crystal Palace | |||
| 24 Jan 2009 | West Bromwich Albion | 2:2 | Burnley | |||
| 24 Jan 2009 | Wolverhampton Wanderers | 1:2 | Middlesbrough | |||
| 25 Jan 2009 | Cardiff City | 0:0 | Arsenal | |||
| 25 Jan 2009 | Liverpool | 1:1 | Everton | |||
| 03 Feb 2009 | Burnley | 3:1 | West Bromwich Albion | replay | ||
| 04 Feb 2009 | Aston Villa | 3:1 | Doncaster Rovers | replay | ||
| 04 Feb 2009 | Blackburn Rovers | 2:1 | Sunderland | replay | ||
| 04 Feb 2009 | Everton | 1:0 | Liverpool | replay | ||
| 04 Feb 2009 | Nottingham Forest | 2:3 | Derby County | replay | ||
| 16 Feb 2009 | Arsenal | 4:0 | Cardiff City | replay | ||
Fifth Round | ||||||
| 14 Feb 2009 | Blackburn Rovers | 2:2 | Coventry City | |||
| 14 Feb 2009 | Sheffield United | 1:1 | Hull City | |||
| 14 Feb 2009 | Swansea City | 1:1 | Fulham | |||
| 14 Feb 2009 | Watford | 1:3 | Chelsea | |||
| 14 Feb 2009 | West Ham United | 1:1 | Middlesbrough | |||
| 15 Feb 2009 | Derby County | 1:4 | Manchester United | |||
| 15 Feb 2009 | Everton | 3:1 | Aston Villa | |||
| 24 Feb 2009 | Coventry City | 1:0 | Blackburn Rovers | replay | ||
| 24 Feb 2009 | Fulham | 2:1 | Swansea City | replay | ||
| 25 Feb 2009 | Middlesbrough | 2:0 | West Ham United | replay | ||
| 26 Feb 2009 | Hull City | 2:1 | Sheffield United | replay | ||
| 08 Mar 2009 | Arsenal | 3:0 | Burnley | |||
Sixth Round | ||||||
| 07 Mar 2009 | Coventry City | 0:2 | Chelsea | |||
| 07 Mar 2009 | Fulham | 0:4 | Manchester United | |||
| 08 Mar 2009 | Everton | 2:1 | Middlesbrough | |||
| 17 Mar 2009 | Arsenal | 2:1 | Hull City | |||
Semi-finals | ||||||
| 18 Apr 2009 | Arsenal | 1:2 | Chelsea | |||
| 19 Apr 2009 | Everton | 0:0 (4:2) | Manchester United | |||
Final | ||||||
| 30 May 2009 | Chelsea | 2:1 | Everton | |||