Chester City
1999-2000
[squad stats] [appearance chart]
| Date | K.O. | Comp | Opponents | Ven | Res | Att | ||||
| Sat 7th Aug | --:-- | FL3 | Barnet | H | L | 0-2 | 2234 |  |
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| Tue 10th Aug | --:-- | LC | Port Vale | H | W | 2-1 | |
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| Sat 14th Aug | --:-- | FL3 | Rotherham United | A | L | 0-4 | 2966 | |
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| Wed 18th Aug | --:-- | FL3 | Northampton Town | H | L | 0-2 | 1904 | |
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| Tue 24th Aug | --:-- | LC | Port Vale | A | D | 4-4 | |
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| Sat 28th Aug | --:-- | FL3 | Torquay United | A | D | 2-2 | 2345 | |
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| Mon 30th Aug | --:-- | FL3 | Rochdale | H | L | 0-2 | 2644 | |
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| Fri 3rd Sep | --:-- | FL3 | Hull City | A | L | 1-2 | 6137 | |
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| Sat 11th Sep | --:-- | FL3 | Exeter City | H | D | 1-1 | 1855 | |
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| Tue 14th Sep | --:-- | LC | Aston Villa | H | L | 0-1 | |
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| Sat 18th Sep | --:-- | FL3 | Brighton and Hove Albion | A | W | 3-2 | 5810 | |
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| Tue 21st Sep | --:-- | LC | Aston Villa | A | L | 0-5 | |
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| Sat 25th Sep | --:-- | FL3 | Lincoln City | H | L | 1-3 | 2161 | |
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| Sat 2nd Oct | --:-- | FL3 | York City | A | D | 2-2 | 2452 | |
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| Sat 9th Oct | --:-- | FL3 | Peterborough United | A | L | 1-2 | 4965 | |
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| Sat 16th Oct | --:-- | FL3 | Macclesfield Town | H | L | 1-2 | 2506 | |
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| Tue 19th Oct | --:-- | FL3 | Cheltenham Town | H | W | 2-1 | 1705 | |
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| Sat 23rd Oct | --:-- | FL3 | Lincoln City | A | L | 1-4 | 3790 | |
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| Sat 30th Oct | --:-- | FAC | Whyteleafe | A | D | 0-0 | |
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| Tue 2nd Nov | --:-- | FL3 | Shrewsbury Town | A | W | 1-0 | 2523 | |
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| Sat 6th Nov | --:-- | FL3 | Plymouth Argyle | H | L | 0-1 | 2027 | |
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| Tue 9th Nov | --:-- | FAC | Whyteleafe | H | W | 3-1 | |
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| Sat 13th Nov | --:-- | FL3 | Hartlepool United | A | L | 0-1 | 2266 | |
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| Sat 20th Nov | --:-- | FAC | Stalybridge Celtic | A | W | 2-1 | |
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| Tue 23rd Nov | --:-- | FL3 | Southend United | H | D | 0-0 | 1906 | |
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| Sat 27th Nov | --:-- | FL3 | Swansea City | H | L | 0-1 | 2713 | |
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| Sat 4th Dec | --:-- | FL3 | Barnet | A | L | 0-2 | 2252 | |
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| Sun 12th Dec | --:-- | FAC | Manchester City | H | L | 1-4 | |
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| Wed 15th Dec | --:-- | FL3 | Darlington | A | L | 1-3 | 3553 | |
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| Sat 18th Dec | --:-- | FL3 | Halifax Town | H | W | 2-1 | 2037 | |
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| Sun 26th Dec | --:-- | FL3 | Mansfield Town | A | L | 1-2 | 3234 | |
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| Tue 28th Dec | --:-- | FL3 | Leyton Orient | H | L | 1-5 | 3160 | |
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| Mon 3rd Jan | --:-- | FL3 | Carlisle United | A | L | 1-4 | 4565 | |
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| Sat 8th Jan | --:-- | FL3 | Darlington | H | L | 1-2 | 2067 | |
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| Tue 11th Jan | --:-- | AMC | Hull City | A | L | 0-2 | |
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| Sat 15th Jan | --:-- | FL3 | Rotherham United | H | L | 0-2 | 3398 | |
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| Sat 22nd Jan | --:-- | FL3 | Northampton Town | A | L | 1-3 | 5332 | |
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| Sat 29th Jan | --:-- | FL3 | Torquay United | H | W | 2-1 | 2229 | |
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| Sat 5th Feb | --:-- | FL3 | Rochdale | A | L | 1-2 | 3093 | |
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| Sat 12th Feb | --:-- | FL3 | Hull City | H | D | 0-0 | 2802 | |
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| Fri 18th Feb | --:-- | FL3 | Swansea City | A | L | 1-2 | 6336 | |
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| Sat 26th Feb | --:-- | FL3 | Brighton and Hove Albion | H | L | 1-7 | 2743 | |
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| Sat 4th Mar | --:-- | FL3 | Exeter City | A | W | 2-0 | 2391 | |
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| Tue 7th Mar | --:-- | FL3 | Plymouth Argyle | A | D | 0-0 | 4140 | |
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| Sat 11th Mar | --:-- | FL3 | Shrewsbury Town | H | D | 0-0 | 4002 | |
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| Sat 18th Mar | --:-- | FL3 | Southend United | A | L | 1-3 | 3483 | |
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| Tue 21st Mar | --:-- | FL3 | Hartlepool United | H | D | 1-1 | 1816 | |
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| Sat 25th Mar | --:-- | FL3 | Mansfield Town | H | W | 5-0 | 1953 | |
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| Sat 1st Apr | --:-- | FL3 | Halifax Town | A | W | 1-0 | 2431 | |
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| Sat 8th Apr | --:-- | FL3 | Carlisle United | H | L | 0-1 | 5507 | |
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| Sat 15th Apr | --:-- | FL3 | Leyton Orient | A | W | 2-1 | 4123 | |
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| Sat 22nd Apr | --:-- | FL3 | Macclesfield Town | A | D | 1-1 | 3456 | |
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| Mon 24th Apr | --:-- | FL3 | York City | H | W | 2-0 | 3503 | |
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| Sat 29th Apr | --:-- | FL3 | Cheltenham Town | A | L | 0-1 | 5391 | |
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| Sat 6th May | --:-- | FL3 | Peterborough United | H | L | 0-1 | 4905 | |