Macclesfield Town
1999-2000
[squad stats] [appearance chart]
| Date | K.O. | Comp | Opponents | Ven | Res | Att | ||||
| Sat 7th Aug | --:-- | FL3 | Northampton Town | H | W | 1-0 | 2694 |  |
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| Tue 10th Aug | --:-- | LC | Stoke City | H | D | 1-1 | |
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| Sat 14th Aug | --:-- | FL3 | Darlington | A | L | 0-3 | 5117 | |
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| Sat 21st Aug | --:-- | FL3 | Swansea City | H | L | 1-2 | 2121 | |
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| Wed 25th Aug | --:-- | LC | Stoke City | A | L | 0-3 | |
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| Sat 28th Aug | --:-- | FL3 | Hull City | A | W | 3-2 | 6222 | |
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| Mon 30th Aug | --:-- | FL3 | Rotherham United | H | D | 1-1 | 2307 | |
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| Sun 5th Sep | --:-- | FL3 | Barnet | A | L | 1-2 | 2426 | |
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| Sat 11th Sep | --:-- | FL3 | Southend United | H | L | 1-2 | 2059 | |
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| Sat 18th Sep | --:-- | FL3 | Lincoln City | A | D | 1-1 | 2918 | |
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| Sat 25th Sep | --:-- | FL3 | Exeter City | A | W | 3-0 | 3202 | |
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| Sat 2nd Oct | --:-- | FL3 | Torquay United | H | L | 1-2 | 2002 | |
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| Sat 9th Oct | --:-- | FL3 | Halifax Town | H | L | 0-2 | 2185 | |
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| Sat 16th Oct | --:-- | FL3 | Chester City | A | W | 2-1 | 2506 | |
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| Tue 19th Oct | --:-- | FL3 | Rochdale | A | W | 1-0 | 2397 | |
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| Sat 23rd Oct | --:-- | FL3 | Exeter City | H | W | 1-0 | 1893 | |
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| Sat 30th Oct | --:-- | FAC | Hull City | H | D | 0-0 | |
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| Tue 2nd Nov | --:-- | FL3 | Mansfield Town | H | W | 5-2 | 1541 | |
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| Sat 6th Nov | --:-- | FL3 | York City | A | W | 2-0 | 2469 | |
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| Tue 9th Nov | --:-- | FAC | Hull City | A | L | 0-4 | |
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| Sun 14th Nov | --:-- | FL3 | Brighton and Hove Albion | H | D | 1-1 | 2920 | |
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| Sat 20th Nov | --:-- | FL3 | Peterborough United | A | D | 2-2 | 5083 | |
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| Sat 27th Nov | --:-- | FL3 | Hartlepool United | H | D | 3-3 | 2351 | |
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| Sat 4th Dec | --:-- | FL3 | Northampton Town | A | L | 0-2 | 5355 | |
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| Sat 11th Dec | --:-- | FL3 | Cheltenham Town | A | D | 1-1 | 3107 | |
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| Sat 18th Dec | --:-- | FL3 | Leyton Orient | H | W | 1-0 | 2303 | |
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| Sun 26th Dec | --:-- | FL3 | Shrewsbury Town | A | W | 1-0 | 4302 | |
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| Tue 28th Dec | --:-- | FL3 | Carlisle United | H | W | 2-1 | 2896 | |
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| Mon 3rd Jan | --:-- | FL3 | Plymouth Argyle | A | L | 2-3 | 6128 | |
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| Sat 8th Jan | --:-- | FL3 | Cheltenham Town | H | L | 1-2 | 3221 | |
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| Tue 11th Jan | --:-- | AMC | Rochdale | A | L | 2-3 | |
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| Sat 15th Jan | --:-- | FL3 | Darlington | H | W | 2-1 | 2399 | |
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| Sat 22nd Jan | --:-- | FL3 | Swansea City | A | L | 0-1 | 6913 | |
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| Sat 29th Jan | --:-- | FL3 | Hull City | H | L | 0-2 | 1900 | |
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| Sat 5th Feb | --:-- | FL3 | Rotherham United | A | L | 1-2 | 4175 | |
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| Sat 12th Feb | --:-- | FL3 | Barnet | H | W | 2-0 | 2114 | |
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| Sat 19th Feb | --:-- | FL3 | Hartlepool United | A | W | 4-1 | 2823 | |
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| Sat 26th Feb | --:-- | FL3 | Lincoln City | H | D | 1-1 | 2445 | |
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| Fri 3rd Mar | --:-- | FL3 | Southend United | A | L | 0-1 | 3725 | |
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| Tue 7th Mar | --:-- | FL3 | York City | H | D | 1-1 | 1581 | |
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| Sat 11th Mar | --:-- | FL3 | Mansfield Town | A | L | 0-1 | 2327 | |
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| Sat 18th Mar | --:-- | FL3 | Peterborough United | H | D | 1-1 | 2309 | |
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| Tue 21st Mar | --:-- | FL3 | Brighton and Hove Albion | A | L | 2-5 | 5596 | |
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| Sat 25th Mar | --:-- | FL3 | Shrewsbury Town | H | W | 4-2 | 1931 | |
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| Sat 1st Apr | --:-- | FL3 | Leyton Orient | A | D | 0-0 | 4302 | |
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| Sat 8th Apr | --:-- | FL3 | Plymouth Argyle | H | W | 4-1 | 2231 | |
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| Sat 15th Apr | --:-- | FL3 | Carlisle United | A | W | 1-0 | 3047 | |
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| Sat 22nd Apr | --:-- | FL3 | Chester City | H | D | 1-1 | 3456 | |
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| Mon 24th Apr | --:-- | FL3 | Torquay United | A | L | 2-3 | 2139 | |
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| Sat 29th Apr | --:-- | FL3 | Rochdale | H | L | 1-2 | 2202 | |
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| Sat 6th May | --:-- | FL3 | Halifax Town | A | W | 1-0 | 2007 | |