| FA Cup | 08/11/08 | Colchester United | - | Leyton Orient | 0:1 |  |
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| League One | 28/12/08 | Colchester United | - | Leyton Orient | 1:0 | ||||
| League One | 11/04/09 | Leyton Orient | - | Colchester United | 2:1 |  |
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| League Cup | 11/08/09 | Colchester United | - | Leyton Orient | 1:2 |  |
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| League One | 10/10/09 | Leyton Orient | - | Colchester United | 0:1 | |
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| League One | 08/05/10 | Colchester United | - | Leyton Orient | 1:0 |
England