Saturday 21st August 1999 | F.A. Challenge Cup Preliminary Round | ||
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Cheadle Town | 0-3 | Warrington Town |
Saturday 25th September 1999 | F.A. Carlsberg Vase 2nd Qualifying Round | ||
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Cheadle Town | 6-0 | Esh Winning |
Saturday 23rd October 1999 | F.A. Carlsberg Vase 1st Round | ||
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Crook Town | 3-1 | Cheadle Town |