Saturday 21st August 1999 | F.A. Challenge Cup Preliminary Round | ||
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Chester-le-Street Town | 1-3 | St Helens Town |
Saturday 4th September 1999 | F.A. Challenge Cup 1st Qualifying Round | ||
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St Helens Town | 1-1 | Pickering Town |
Tuesday 7th September 1999 | F.A. Challenge Cup 1st Qualifying Round Replay | ||
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Pickering Town | 3-2 | St Helens Town |
Saturday 25th September 1999 | F.A. Carlsberg Vase 2nd Qualifying Round | ||
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Selby Town | 4-1 | St Helens Town |