| 3. Round | 14/01/2009 | Southend United | - | Chelsea FC | 1:4 | ||||
| 4. Round | 24/01/2009 | Chelsea FC | - | Ipswich Town | 3:1 | ||||
| Quarter-finals | 07/03/2009 | Coventry City | - | Chelsea FC | 0:2 | ||||
| Final | 30/05/2009 | Chelsea FC | - | Everton FC | 2:1 |
| 3. Round | 14/01/2009 | Southend United | - | Chelsea FC | 1:4 | ||||
| 4. Round | 24/01/2009 | Chelsea FC | - | Ipswich Town | 3:1 | ||||
| Quarter-finals | 07/03/2009 | Coventry City | - | Chelsea FC | 0:2 | ||||
| Final | 30/05/2009 | Chelsea FC | - | Everton FC | 2:1 |
| José Bosingwa da Silva | |
| Born: | 24.08.1982 |
| Place of birth: |
Mbandaka, 
Congo DR |
| Nationality: |
Portugal
Congo DR |
| Height: | 183 cm |
| Weight: | 75 kg |
| Position(s): | Right Back Right Midfielder |
| Foot: | right |
