| Round of 16 | 14/02/2009 | West Ham United | - | Middlesbrough FC | 1:1 | ||||
| Round of 16 | 25/02/2009 | Middlesbrough FC | - | West Ham United | 2:0 |
| Round of 16 | 14/02/2009 | West Ham United | - | Middlesbrough FC | 1:1 | ||||
| Round of 16 | 25/02/2009 | Middlesbrough FC | - | West Ham United | 2:0 |
| Matthew James Upson | |
| Born: | 18.04.1979 |
| Place of birth: |
Suffolk, 
England |
| Nationality: |
England
|
| Height: | 185 cm |
| Weight: | 72 kg |
| Position(s): | Centre Back |
| Foot: | left |