| F.A. Cup Matches |
| |  | | | |
| 15 Nov 2008: Round 1
|
| Brentford | | vs. | | Chester |
| Bury | | vs. | | Macclesfield |
| Hereford | | vs. | | Morecambe |
| Mansfield Town | | vs. | | Peterborough |
| Notts County | | vs. | | Rochdale |
| Shrewsbury | | vs. | | Barnet |
| Stockp. County | | vs. | | Rotherham |
| Wycombe | | vs. | | Accrington |
| | | | | |
| 6 Dec 2008: Round 2
|
| Barnsley | | vs. | | Port Vale |
| Bournemouth | | vs. | | Grimsby Town |
| Bradford City | | vs. | | Gillingham |
| Chesterfield | | vs. | | Doncaster |
| Dagenh. Redbr. | | vs. | | Walsall |
| Hartlepool | | vs. | | Carlisle United |
| Lincoln City | | vs. | | Darlington |
| Luton Town | | vs. | | Cheltenh. Town |
| Northampton | | vs. | | Crewe |
| Nott. Forest | | vs. | | Huddersfield |
| Plymouth Argyle | | vs. | | Millwall |
| Stoke City | | vs. | | Brighton |
| Swansea City | | vs. | | Bristol Rovers |
| Swindon Town | | vs. | | MK Dons |
| Tranmere | | vs. | | Wrexham |
| Yeovil | | vs. | | Leyton Orient |
| [TBD] | | vs. | | [TBD] |
| [TBD] | | vs. | | [TBD] |
| [TBD] | | vs. | | [TBD] |
| [TBD] | | vs. | | [TBD] |
| | | | | |
| 10 Jan 2009: Round 3
|
| Bristol City | | vs. | | Aston Villa |
| Burnley | | vs. | | Leeds United |
| Cardiff City | | vs. | | Blackburn |
| Charlton | | vs. | | Middlesbrough |
| Chelsea FC | | vs. | | Port Vale or Barnsley |
| Coventry City | | vs. | | Huddersfield or Nott. Forest |
| Everton | | vs. | | Tranmere or Wrexham |
| Fulham | | vs. | | Norwich |
| Leicester City | | vs. | | [TBD] |
| Liverpool | | vs. | | [TBD] |
| Manchester City | | vs. | | Reading |
| Manchester Utd | | vs. | | Arsenal FC |
| Oldham Athletic | | vs. | | Wolverhampton |
| Portsmouth | | vs. | | West Brom |
| Preston | | vs. | | Bradford City or Gillingham |
| QPR | | vs. | | Bristol Rovers or Swansea City |
| Scunthorpe Utd | | vs. | | Bolton |
| Sheffield Utd | | vs. | | Ipswich Town |
| Southampton | | vs. | | [TBD] |
| Southend Utd | | vs. | | Yeovil or Leyton Orient |
| Sunderland | | vs. | | Crystal Palace |
| Tottenham | | vs. | | Carlisle United or Hartlepool |
| Walsall or Dagenh. Redbr. | | vs. | | West Ham |
| Bournemouth or Grimsby Town | | vs. | | Derby County |
| Chesterfield or Doncaster | | vs. | | Colchester Utd |
| Brighton or Stoke City | | vs. | | Birmingham |
| Swindon Town or MK Dons | | vs. | | Blackpool |
| Millwall or Plymouth Argyle | | vs. | | Watford |
| Northampton or Crewe | | vs. | | Hull City |
| [TBD] | | vs. | | Sheff Wed |
| Darlington or Lincoln City | | vs. | | Wigan Athletic |
| Cheltenh. Town or Luton Town | | vs. | | Newcastle |
| | | | | |
| 31 Jan 2009: Round 4
|
| [TBD] | | vs. | | [TBD] |
| [TBD] | | vs. | | [TBD] |
| [TBD] | | vs. | | [TBD] |
| [TBD] | | vs. | | [TBD] |
| [TBD] | | vs. | | [TBD] |
| [TBD] | | vs. | | [TBD] |
| [TBD] | | vs. | | [TBD] |
| [TBD] | | vs. | | [TBD] |
| [TBD] | | vs. | | [TBD] |
| [TBD] | | vs. | | [TBD] |
| [TBD] | | vs. | | [TBD] |
| [TBD] | | vs. | | [TBD] |
| [TBD] | | vs. | | [TBD] |
| [TBD] | | vs. | | [TBD] |
| [TBD] | | vs. | | [TBD] |
| [TBD] | | vs. | | [TBD] |
| | | | | |
| 21 Feb 2009: Round 5
|
| [TBD] | | vs. | | [TBD] |
| [TBD] | | vs. | | [TBD] |
| [TBD] | | vs. | | [TBD] |
| [TBD] | | vs. | | [TBD] |
| [TBD] | | vs. | | [TBD] |
| [TBD] | | vs. | | [TBD] |
| [TBD] | | vs. | | [TBD] |
| [TBD] | | vs. | | [TBD] |
| | | | | |
| 14 Mar 2009: Quarter-Final
|
| [TBD] | | vs. | | [TBD] |
| [TBD] | | vs. | | [TBD] |
| [TBD] | | vs. | | [TBD] |
| [TBD] | | vs. | | [TBD] |
| | | | | |
| 12 Apr 2009: Semi-Final
|
| [TBD] | | vs. | | [TBD] |
| [TBD] | | vs. | | [TBD] |
| | | | | |
| 23 May 2009: Final
|
| [TBD] | | vs. | | [TBD] |