| Shanklin | | 2005 | | 1st Qualifying Round | 11-09-2005 | | Shanklin | St Peter's | 2-0 | | 2nd Qualifying Round | 25-09-2005 | | Shanklin | AFC Bournemouth | 1-1 | | First Round | 23-10-2005 | | Keynsham Town | Shanklin | 4-1 | |
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| 2008 | | Preliminary Round | 07-09-2008 | | Abbey Rangers | Shanklin | 0-18 | | 1st Qualifying Round | 28-09-2008 | | Shanklin | Horley Town | 1-1 | |
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| 2009 | | 1st Qualifying Round | 27-09-2009 | | BTC Southampton | Shanklin | O-W | | 2nd Qualifying Round | 11-10-2009 | | Shanklin | Bracknell Town | 5-0 | | 3rd Qualifying Round | 25-10-2009 | | Shanklin | Oxford United | 1-0 | | First Round | 08-11-2009 | | Shanklin | Havant & Waterlooville | 0-2 | |
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| 2010 | | 2nd Qualifying Round | 24-10-2010 | | Shanklin | Andover New Street | 1-3 | | 2011 | | 1st Qualifying Round | 02-10-2011 | | Shanklin | Broadstone | 12-0 | | 2nd Qualifying Round | 23-10-2011 | | Christchurch | Shanklin | 0-6 | | 3rd Qualifying Round | 13-11-2011 | | Yeovil Town | Shanklin | 1-2 | | First Round | 11-12-2011 | | Shanklin | Parley Sports | 3-1 | | Second Round | 08-01-2012 | | Larkhall Athletic | Shanklin | 2-1 | |
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| 2012 | | 1st Qualifying Round | 30-09-2012 | | Parley Sports | Shanklin | 1-5 | | 2nd Qualifying Round | 14-10-2012 | | Shanklin | Andover New Street | 2-0 | | 3rd Qualifying Round | 11-11-2012 | | Shanklin | Brislington | 1-3 | | 2013 | | 3rd Qualifying Round | 03-11-2013 | | Shanklin | Gosport Borough | 0-1 | | 2014 | | 3rd Qualifying Round | 02-11-2014 | | Maidenhead United | Shanklin | 3-0 | | 2015 | | 3rd Qualifying Round | 11-10-2015 | | AEK-BOCO | Shanklin | 1-0 | | 2016 | | 3rd Qualifying Round | 09-10-2016 | | Shanklin | St Nicholas | 3-2 | | Fourth Qualifying Round | 13-11-2016 | | Shanklin | Southampton | 0-3 | | 2018 | | 1st Qualifying Round | 02-09-2018 | | Shanklin | New Milton Town | 0-3 | | 2019 | | Preliminary Round | 01-09-2019 | | Shanklin | Alton | 1-0 | | 1st Qualifying Round | 22-09-2019 | | Shanklin | Sherborne Town | 0-12 | | 2020 | | Preliminary Round | 20-09-2020 | | Shanklin | Moneyfields | 0-8 | | 2021 | | 1st Qualifying Round | 12-09-2021 | | QK Southampton | Shanklin | 4-5 | | 2nd Qualifying Round | 03-10-2021 | | Shanklin | Bournemouth Sports | 0-2 | |
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| 2022 | | 1st Qualifying Round | 18-09-2022 | | Shanklin | AFC Stoneham | 1-3 | | 2023 | | 1st Qualifying Round | 10-09-2023 | | Fleet Town | Shanklin | 2-8 | | 2nd Qualifying Round | 01-10-2023 | | Shanklin | Winchester City Flyers | 2-6 | | 2024 | | 2nd Qualifying Round | 22-09-2024 | | Shanklin | AFC Stoneham | 1-5 |
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