| Dudley United | | 2004 | | First Qualifying Round | 05-09-2004 | | Dudley United | Stratford Town | 0-5 | | 2005 | | First Qualifying Round | 11-09-2005 | | Cambridge Rangers | Dudley United | 1-5 | | Second Qualifying Round | 25-09-2005 | | Dudley United | Lichfield Diamonds | 2-3 | | 2006 | | Preliminary Round | 10-09-2006 | | Dudley United | Walsall | 2-3 | | 2007 | | First Qualifying Round | 16-09-2007 | | Solihull | Dudley United | 4-1 | | 2008 | | First Qualifying Round | 28-09-2008 | | Stratford Town | Dudley United | 0-3 | | Second Qualifying Round | 12-10-2008 | | Dudley United | Tamworth Lionesses | 3-1 | | Third Qualifying Round | 26-10-2008 | | Lichfield Diamonds | Dudley United | 1-1 | |
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| 2009 | | First Qualifying Round | 27-09-2009 | | Lichfield Diamonds | Dudley United | 1-6 | | Second Qualifying Round | 11-10-2009 | | Hereford Pegasus | Dudley United | 2-5 | | Third Qualifying Round | 25-10-2009 | | Dudley United | Sandiacre Town | 2-1 | | Second Round | 29-11-2009 | | Cambridge United | Dudley United | 2-1 | |
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| 2011 | | Third Qualifying Round | 13-11-2011 | | AFC Trinity | Dudley United | W/O | |
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