| 1. Round | 06/11/2010 | Dagenham & Redbridge | - | Leyton Orient | 1:1 | ||||
| 1. Round | 16/11/2010 | Leyton Orient | - | Dagenham & Redbridge | 3:2 | ||||
| 2. Round | 29/11/2010 | Droylsden FC | - | Leyton Orient | 1:1 | ||||
| 2. Round | 07/12/2010 | Leyton Orient | - | Droylsden FC | 8:2 aet | ||||
| 3. Round | 08/01/2011 | Norwich City | - | Leyton Orient | 0:1 | ||||
| 4. Round | 29/01/2011 | Swansea City | - | Leyton Orient | 1:2 | ||||
| Round of 16 | 02/03/2011 | Arsenal FC | - | Leyton Orient | 5:0 |
England