| 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 | ||||
| Quarter-finals | 08/03/2009 | Everton FC | - | Middlesbrough FC | 2:1 |
| 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 | ||||
| Quarter-finals | 08/03/2009 | Everton FC | - | Middlesbrough FC | 2:1 |
| Julio Andrés Arca | |
| Born: | 31.01.1981 |
| Place of birth: |
Quilmes, Buenos Aires, 
Argentina |
| Nationality: |
Argentina
Italy |
| Height: | 185 cm |
| Weight: | 70 kg |
| Position(s): | Central Midfielder Left Back |
| Foot: | left |