| Chester-le-Street | | 1996 | | First Round | 29-09-1996 | | Newcastle | Chester-le-Street | 0-1 | | Second Round | 03-11-1996 | | Middlesbrough | Chester-le-Street | W/O | |
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| 1997 | | First Round | 28-09-1997 | | Chester-le-Street | Leeds United | 3-8 | | 2000 | | First Round | 29-10-2000 | | Chester-le-Street | Three Bridges | W/O | | Second Round | 12-11-2000 | | Chester-le-Street | Billingham | 5-3 | | Third Round | 10-12-2000 | | Chester-le-Street | Sheffield Wednesday | 2-0 | | Fourth Round | 07-01-2001 | | Newport County | Chester-le-Street | 3-3 | | Fifth Round | 28-01-2001 | | Bristol Rovers | Chester-le-Street | 4-3 | |
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| 2001 | | First Round | 28-10-2001 | | Chester-le-Street | Blackpool Wren Rovers | 0-1 | | 2003 | | First Qualifying Round | 07-09-2003 | | Kirklees | Chester-le-Street | 0-13 | | Second Qualifying Round | 28-09-2003 | | Chester-le-Street | Lumley | 3-1 | | 2005 | | First Round | 23-10-2005 | | Doncaster Parkland Rovers | Chester-le-Street | 0-2 | | Second Round | 13-11-2005 | | Blyth Spartans | Chester-le-Street | 3-2 | |
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