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| Last 10 games | more | |||
| 04.10.2008 | PR Premier League | Wigan | Middlesbrough | 0-1 |
| 27.09.2008 | PR Premier League | Middlesbrough | West Bromwich | 0-1 |
| 23.09.2008 | LC Round 3 | Manchester United | Middlesbrough | 3-1 |
| 20.09.2008 | PR Premier League | Sunderland | Middlesbrough | 2-0 |
| 13.09.2008 | PR Premier League | Portsmouth | Middlesbrough | 2-1 |
| 30.08.2008 | PR Premier League | Middlesbrough | Stoke City | 2-1 |
| 26.08.2008 | LC Round 2 | Middlesbrough | Yeovil Town | 5-1 |
| 23.08.2008 | PR Premier League | Liverpool | Middlesbrough | 2-1 |
| 16.08.2008 | PR Premier League | Middlesbrough | Tottenham | 2-1 |
| 08.08.2008 | CF Club Friendly | Sparta Rotterdam | Middlesbrough | 1-6 |
| Next 10 games | more | |||
| 18.10.2008 | PR Premier League | Middlesbrough | Chelsea FC |  |
| 25.10.2008 | PR Premier League | Blackburn Rovers | Middlesbrough | |
| 28.10.2008 | PR Premier League | Middlesbrough | Manchester City | |
| 01.11.2008 | PR Premier League | Middlesbrough | West Ham | |
| 08.11.2008 | PR Premier League | Aston Villa FC | Middlesbrough | |
| 16.11.2008 | PR Premier League | Everton FC | Middlesbrough | |
| 22.11.2008 | PR Premier League | Middlesbrough | Bolton Wanderers | |
| 29.11.2008 | PR Premier League | Middlesbrough | Newcastle | |
| 06.12.2008 | PR Premier League | Hull City | Middlesbrough | |
| 13.12.2008 | PR Premier League | Middlesbrough | Arsenal FC | |