| Kettering Town | | 2003 | | First Qualifying Round | 07-09-2003 | | Birstall United | Kettering Town | 2-1 | | 2004 | | Second Qualifying Round | 26-09-2004 | | Buxton | Kettering Town | 2-0 | | 2005 | | First Qualifying Round | 11-09-2005 | | Kettering Town | Birstall FL&E | 5-4 | | Second Qualifying Round | 25-09-2005 | | Rushcliffe Eagles | Kettering Town | 1-2 | | First Round | 23-10-2005 | | Ipswich Town | Kettering Town | 7-0 | | 2006 | | First Qualifying Round | 24-09-2006 | | Rothwell Town | Kettering Town | 2-5 | | Second Qualifying Round | 08-10-2006 | | Cottenham United | Kettering Town | 0-8 | | First Round | 29-10-2006 | | Kettering Town | Rushden & Diamonds | 0-5 | | 2007 | | First Qualifying Round | 16-09-2007 | | Bedford | Kettering Town | 3-2 | | 2008 | | Preliminary Round | 07-09-2008 | | Kettering Town | Woodford United | 11-0 | | First Qualifying Round | 28-09-2008 | | Kettering Town | Bedford | 0-1 | | 2009 | | First Qualifying Round | 27-09-2009 | | Kettering Town | Hitchin Hearts | 3-0 | | Second Qualifying Round | 11-10-2009 | | Kettering Town | Leighton Linslade | 2-1 | | Third Qualifying Round | 25-10-2009 | | Kettering Town | Barking | 1-5 | | 2010 | | Second Qualifying Round | 24-10-2010 | | Raunds Town | Kettering Town | 1-8 | | Third Qualifying Round | 14-11-2010 | | Kettering Town | Woodbridge Town | 0-1 | | 2011 | | First Qualifying Round | 02-10-2011 | | Kettering Town | Peterborough Hampton | 10-0 | | Second Qualifying Round | 23-10-2011 | | Kettering Town | Peterborough Sports | 0-5 | | 2013 | | First Qualifying Round | 22-09-2013 | | Kettering Town | Bedford | 2-6 | | 2014 | | Preliminary Round | 07-09-2014 | | Raunds Town | Kettering Town | 4-2 | |
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| 2015 | | First Qualifying Round | 06-09-2015 | | Kettering Town | Rothwell Corinthians | 5-0 | | Second Qualifying Round | 20-09-2015 | | Kettering Town | Sandy | 5-0 | | Third Qualifying Round | 11-10-2015 | | Stone Dominoes | Kettering Town | 3-2 | |
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| 2016 | | Second Qualifying Round | 18-09-2016 | | Kettering Town | Thrapston Town | 4-0 | | Third Qualifying Round | 09-10-2016 | | Kettering Town | Brandon Town | 6-0 | | Fourth Qualifying Round | 13-11-2016 | | Kettering Town | Peterborough Northern Star | 0-3 | | 2017 | | First Qualifying Round | 03-09-2017 | | Kettering Town | Woodford United | 10-0 | | Second Qualifying Round | 17-09-2017 | | Cambridge City | Kettering Town | 5-2 | | 2018 | | First Qualifying Round | 02-09-2018 | | Kettering Town | Acle United | 1-3 | | 2019 | | Preliminary Round | 01-09-2019 | | Wroxham | Kettering Town | 6-2 | | 2020 | | Extra Preliminary Round | 06-09-2020 | | Wroxham | Kettering Town | 10-0 | | 2021 | | First Qualifying Round | 12-09-2021 | | Sherwood | Kettering Town | 0-3 | | Second Qualifying Round | 03-10-2021 | | Notts County | Kettering Town | 2-0 | | 2022 | | First Qualifying Round | 11-09-2022 | | Kettering Town | Sleaford United | W/O | | Second Qualifying Round | 02-10-2022 | | Desborough | Kettering Town | 0-5 | | Third Qualifying Round | 23-10-2022 | | Dronfield Town | Kettering Town | 1-0 | | 2023 | | First Qualifying Round | 10-09-2023 | | Kettering Town | Long Buckby AFC | 7-0 | | First Qualifying Round | 10-09-2023 | | Ruston Sports | Kettering Town | 0-7 | | Second Qualifying Round | 01-10-2023 | | Mansfield Town | Kettering Town | 1-1 | |
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