| Coventry Development | | 2009 | | First Qualifying Round | 27-09-2009 | | Crusaders | Coventry Development | O-W | | Second Qualifying Round | 11-10-2009 | | Corby Stewarts & Lloyds | Coventry Development | 4-0 | |
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| 2012 | | First Qualifying Round | 30-09-2012 | | Coventry Development | Walsall | 2-3 | | 2014 | | First Qualifying Round | 28-09-2014 | | Kenilworth Town | Coventry Development | 1-0 | | 2015 | | Second Qualifying Round | 20-09-2015 | | Coventry Development | Bedworth United | 3-2 | | Third Qualifying Round | 11-10-2015 | | Coventry Development | Shrewsbury Town | 5-0 | | Fourth Qualifying Round | 08-11-2015 | | Coventry Development | Stone Dominoes | 1-3 | | 2016 | | Second Qualifying Round | 18-09-2016 | | Coleshill Town | Coventry Development | 0-3 | | Third Qualifying Round | 09-10-2016 | | Arnold Town | Coventry Development | 3-3 | | Fourth Qualifying Round | 13-11-2016 | | Long Eaton United | Coventry Development | 7-1 | |
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