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| Last 10 games | more | |||
| 16.08.2008 | PR Premier League | Middlesbrough | Tottenham | 2-1 |
| 08.08.2008 | CF Club Friendly | Sparta Rotterdam | Middlesbrough | 1-6 |
| 05.08.2008 | CF Club Friendly | Darlington FC | Middlesbrough | 0-5 |
| 02.08.2008 | CF Club Friendly | Hibernian | Middlesbrough | 2-3 |
| 29.07.2008 | CF Club Friendly | Carlisle United | Middlesbrough | 1-2 |
| 24.07.2008 | CF Club Friendly | Guimaraes | Middlesbrough | 1-0 |
| 22.07.2008 | CF Club Friendly | Celtic | Middlesbrough | 1-1 |
| 18.07.2008 | CF Club Friendly | York City | Middlesbrough | 2-2 |
| 11.05.2008 | PR Premier League | Middlesbrough | Manchester City | 8-1 |
| 03.05.2008 | PR Premier League | Middlesbrough | Portsmouth | 2-0 |
| Next 10 games | more | |||
| 23.08.2008 | PR Premier League | Liverpool | Middlesbrough |  |
| 26.08.2008 | LC Round 2 | Middlesbrough | Yeovil Town | |
| 30.08.2008 | PR Premier League | Middlesbrough | Stoke City | |
| 13.09.2008 | PR Premier League | Portsmouth | Middlesbrough | |
| 20.09.2008 | PR Premier League | Sunderland | Middlesbrough | |
| 27.09.2008 | PR Premier League | Middlesbrough | West Bromwich | |
| 04.10.2008 | PR Premier League | Wigan | Middlesbrough | |
| 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 | |