| Leyton Orient | | 2003 | | Second Qualifying Round | 28-09-2003 | | Leyton Orient | Tring Athletic | 6-0 | | First Round | 26-10-2003 | | Leyton Orient | Woking | 2-1 | | Second Round | 09-11-2003 | | Leyton Orient | Colchester United | 3-1 | | Third Round | 07-12-2003 | | Leyton Orient | Ipswich Town | 4-2 | | Fourth Round | 04-01-2004 | | Lincoln City | Leyton Orient | 1-3 | | Fifth Round | 25-01-2004 | | Leyton Orient | Birmingham City | 1-6 | | 2004 | | First Round | 24-10-2004 | | Leyton Orient | Queens Park Rangers | 0-1 | | 2005 | | First Round | 23-10-2005 | | Gillingham | Leyton Orient | 1-2 | | Second Round | 13-11-2005 | | Leyton Orient | Hastings United | 5-3 | | Third Round | 04-12-2005 | | Brighton & Hove Albion | Leyton Orient | 3-0 | |
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| 2006 | | First Round | 29-10-2006 | | Dagenham & Redbridge | Leyton Orient | 3-4 | | Second Round | 12-11-2006 | | Leyton Orient | Langford | 0-2 |
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