| Penzance | | 1999 | | Extra Preliminary Round | 12-09-1999 | | Bristol United | Penzance | 1-2 | | Preliminary Round | 26-09-1999 | | Penzance | Red Star Southampton | 0-1 | | 2000 | | Extra Preliminary Round | 10-09-2000 | | Wendron | Penzance | 0-8 | | Preliminary Round | 24-09-2000 | | Penzance | Cogan Coronation | 2-1 | | First Round | 29-10-2000 | | Southampton | Penzance | 3-1 | | 2001 | | 1st Qualifying Round | 09-09-2001 | | Newquay | Penzance | 4-2 | | 2002 | | 1st Qualifying Round | 08-09-2002 | | Penzance | Newquay | 2-6 | |
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| 2003 | | 1st Qualifying Round | 07-09-2003 | | Penzance | Newquay | 3-1 | | 2nd Qualifying Round | 28-09-2003 | | Penzance | Swindon Spitfires | 4-0 | | First Round | 26-10-2003 | | Yeovil Town | Penzance | 0-1 | | Second Round | 09-11-2003 | | Penzance | Forest Green Rovers | 1-2 | |
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| 2004 | | 1st Qualifying Round | 05-09-2004 | | Ross Town | Penzance | 4-3 | | 2005 |  | | 1st Qualifying Round | 11-09-2005 | | Launceston | Penzance | 2-4 | | 2nd Qualifying Round | 25-09-2005 | | Penzance | Saltash United | 11-0 | | First Round | 23-10-2005 | | Penzance | Winscombe | 2-1 | | Second Round | 13-11-2005 | | Hereford Pegasus | Penzance | 3-0 | |
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| 2006 | | 1st Qualifying Round | 24-09-2006 | | Penzance | Tetbury Town | 7-1 | | 2nd Qualifying Round | 08-10-2006 | | Holway United | Penzance | 1-2 | | First Round | 29-10-2006 | | Penzance | Swindon Town | 4-2 | | Second Round | 12-11-2006 | | Forest Green Rovers | Penzance | 3-1 | |
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| 2007 | | Preliminary Round | 02-09-2007 | | Penzance | Launceston | 7-1 | | 1st Qualifying Round | 16-09-2007 | | Penzance | Saltash United | 8-1 | | 2nd Qualifying Round | 30-09-2007 | | Penzance | Larkhall Athletic | 6-0 | | 3rd Qualifying Round | 07-10-2007 | | Cullompton Rangers | Penzance | 3-3 | | First Round | 28-10-2007 | | Frome Town | Penzance | 2-0 | |
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