2. Round | 16/08/2008 | Peterborough United | - | Leyton Orient | 3:0 | ||||
3. Round | 23/08/2008 | Leyton Orient | - | Carlisle United | 0:0 | ||||
4. Round | 30/08/2008 | Brighton & Hove Albion | - | Leyton Orient | 0:0 | ||||
5. Round | 06/09/2008 | Walsall FC | - | Leyton Orient | 0:2 | ||||
6. Round | 13/09/2008 | Leyton Orient | - | Stockport County | 0:3 | ||||
7. Round | 20/09/2008 | Leyton Orient | - | Leicester City | 1:3 | ||||
8. Round | 26/09/2008 | Southend United | - | Leyton Orient | 3:0 | ||||
9. Round | 04/10/2008 | Leyton Orient | - | Scunthorpe United | 2:2 | ||||
12. Round | 21/10/2008 | Leeds United | - | Leyton Orient | 2:1 | ||||
19. Round | 06/12/2008 | Northampton Town | - | Leyton Orient | 1:1 |