Saturday 21st August 1999 | F.A. Challenge Cup Preliminary Round | ||
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Woodley Sports | 2-1 | Ossett Albion |
Saturday 4th September 1999 | F.A. Challenge Cup 1st Qualifying Round | ||
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Liversedge | 3-2 | Woodley Sports |
Saturday 11th September 1999 | F.A. Carlsberg Vase 1st Qualifying Round | ||
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Woodley Sports | 0-3 | Billingham Synthonia |