| Manager Mode Summary | Fixtures/Results | League Tables | Stats Leaders | Team Details |
| Fixtures: | Wycombe | Full List | Football League Champ | EFA |
| English Cup | League Cup |
| English Cup Matches | |||||
| 15 Nov 2008: Round 1 | |||||
| Accrington | 1 - 0 | Swindon Town | |||
| Barnet | 2 - 0 | Torquay | |||
| Chester | 1 - 1 | Hereford | |||
| (2 - 3 pen.) | |||||
| Hartlepool | 0 - 2 | Boston | |||
| MK Dons | 3 - 1 | Macclesfield | |||
| Rochdale | 2 - 0 | Stockp. County | |||
| Walsall | 1 - 0 | Mansfield Town | |||
| Wrexham | 0 - 1 | Bury | |||
| 6 Dec 2008: Round 2 | |||||
| Accrington | 0 - 2 | MK Dons | |||
| Barnsley | 0 - 2 | Blackpool | |||
| Bradford City | 1 - 3 | Millwall | |||
| Bristol Rovers | 1 - 0 | Plymouth Argyle | |||
| Cheltenham Town | 0 - 3 | Brentford | |||
| Chesterfield | 1 - 2 | Crewe | |||
| Colchester Utd | 1 - 2 | Nott. Forest | |||
| Darlington | 0 - 1 | Northampton | |||
| Doncaster | 1 - 3 | Tranmere Rovers | |||
| Gillingham | 0 - 3 | Carlisle United | |||
| Hereford | 1 - 1 | Bury | |||
| (4 - 5 pen.) | |||||
| Lincoln City | 2 - 2 | Leyton Orient | |||
| (4 - 5 pen.) | |||||
| Oldham Athletic | 0 - 3 | Bournemouth | |||
| Port Vale | 0 - 3 | Brighton | |||
| Rochdale | 1 - 4 | Barnet | |||
| Rotherham | 1 - 2 | Notts County | |||
| Shrewsbury | 0 - 0 | Peterborough | |||
| (4 - 3 pen.) | |||||
| Swansea City | 2 - 3 | Grimsby Town | |||
| Walsall | 2 - 3 | Boston | |||
| Yeovil | 0 - 4 | Southend United | |||
| 10 Jan 2009: Round 3 | |||||
| Arsenal | 2 - 4 | Hull City | |||
| Birmingham | 2 - 2 | Cardiff City | |||
| (0 - 3 pen.) | |||||
| Bristol Rovers | 0 - 0 | Derby County | |||
| (3 - 0 pen.) | |||||
| Burnley | 3 - 2 | Brighton | |||
| Bury | 0 - 4 | Bolton | |||
| Carlisle United | 2 - 0 | Bristol City | |||
| Charlton | 2 - 1 | Bournemouth | |||
| Coventry City | 1 - 3 | Nott. Forest | |||
| Crystal Palace | 0 - 1 | Middlesbrough | |||
| Everton | 0 - 2 | Tottenham | |||
| Fulham | 1 - 0 | Barnet | |||
| Huddersfield | 0 - 2 | Aston Villa | |||
| Leeds United | 1 - 2 | Stoke City | |||
| Leicester City | 1 - 1 | Brentford | |||
| (3 - 2 pen.) | |||||
| Leyton Orient | 1 - 0 | Wolverhampton | |||
| Liverpool | 0 - 1 | West Brom | |||
| Manchester City | 3 - 0 | Blackpool | |||
| Northampton | 1 - 2 | Chelsea | |||
| Norwich | 3 - 2 | Boston | |||
| Notts County | 0 - 4 | Manchester Utd | |||
| Portsmouth | 0 - 0 | Millwall | |||
| (4 - 2 pen.) | |||||
| Reading | 1 - 2 | QPR | |||
| Scunthorpe Utd | 0 - 3 | Preston | |||
| Sheff Wed | 0 - 1 | Grimsby Town | |||
| Sheffield Utd | 2 - 1 | Crewe | |||
| Southampton | 4 - 1 | Shrewsbury | |||
| Southend United | 3 - 4 | Ipswich Town | |||
| Tranmere Rovers | 1 - 3 | Sunderland | |||
| Watford | 1 - 2 | Blackburn | |||
| West Ham | 0 - 0 | Newcastle | |||
| (2 - 3 pen.) | |||||
| Wigan Athletic | 1 - 0 | MK Dons | |||
| Wycombe | 2 - 1 | Luton Town | |||
| 31 Jan 2009: Round 4 | |||||
| Aston Villa | 2 - 3 | Wycombe | |||
| Blackburn | 5 - 0 | QPR | |||
| Burnley | 1 - 1 | Carlisle United | |||
| (3 - 4 pen.) | |||||
| Charlton | 1 - 0 | Sheffield Utd | |||
| Fulham | 0 - 0 | Bolton | |||
| (4 - 3 pen.) | |||||
| Grimsby Town | 0 - 1 | Portsmouth | |||
| Ipswich Town | 0 - 1 | Bristol Rovers | |||
| Leicester City | 0 - 0 | Sunderland | |||
| (2 - 3 pen.) | |||||
| Leyton Orient | 0 - 1 | Chelsea | |||
| Manchester City | 2 - 1 | Manchester Utd | |||
| Middlesbrough | 2 - 1 | Hull City | |||
| Newcastle | 1 - 0 | West Brom | |||
| Nott. Forest | 3 - 1 | Southampton | |||
| Preston | 2 - 0 | Cardiff City | |||
| Tottenham | 2 - 0 | Stoke City | |||
| Wigan Athletic | 2 - 0 | Norwich | |||
| 21 Feb 2009: Round 5 | |||||
| Blackburn | 3 - 0 | Tottenham | |||
| Charlton | 0 - 0 | Bristol Rovers | |||
| (2 - 4 pen.) | |||||
| Chelsea | 1 - 0 | Nott. Forest | |||
| Fulham | 1 - 1 | Wigan Athletic | |||
| (2 - 3 pen.) | |||||
| Manchester City | 1 - 0 | Carlisle United | |||
| Middlesbrough | 1 - 1 | Newcastle | |||
| (4 - 2 pen.) | |||||
| Sunderland | 2 - 3 | Portsmouth | |||
| Wycombe | 4 - 0 | Preston | |||
| 14 Mar 2009: Quarter-Final | |||||
| Bristol Rovers | 0 - 5 | Manchester City | |||
| Portsmouth | 0 - 1 | Chelsea | |||
| Wigan Athletic | 1 - 2 | Blackburn | |||
| Wycombe | 3 - 1 | Middlesbrough | |||
| 12 Apr 2009: Semi-Final | |||||
| Manchester City | 0 - 0 | Chelsea | |||
| (4 - 2 pen.) | |||||
| Wycombe | 0 - 0 | Blackburn | |||
| (4 - 2 pen.) | |||||
| 23 May 2009: Final | |||||
| Wycombe | vs. | Manchester City | |||
| Manager Mode Summary | Fixtures/Results | League Tables | Stats Leaders | Team Details |
| Fixtures: | Wycombe | Full List | Football League Champ | EFA |
| English Cup | League Cup |