Cheltenham Town
1999-2000
[squad stats] [appearance chart]
| Date | K.O. | Comp | Opponents | Ven | Res | Att | ||||
| Sat 7th Aug | --:-- | FL3 | Rochdale | H | L | 0-2 | 5189 |  |
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| Tue 10th Aug | --:-- | LC | Norwich City | A | L | 0-2 | |
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| Sat 14th Aug | --:-- | FL3 | Mansfield Town | A | W | 1-0 | 2348 | |
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| Sat 21st Aug | --:-- | FL3 | Hull City | H | W | 1-0 | 4427 | |
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| Tue 24th Aug | --:-- | LC | Norwich City | H | W | 2-1 | |
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| Sat 28th Aug | --:-- | FL3 | Hartlepool United | A | W | 1-0 | 2390 | |
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| Mon 30th Aug | --:-- | FL3 | Barnet | H | L | 1-2 | 3518 | |
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| Sun 12th Sep | --:-- | FL3 | Shrewsbury Town | H | L | 0-1 | 3704 | |
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| Sat 18th Sep | --:-- | FL3 | Peterborough United | A | L | 0-1 | 5943 | |
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| Sat 25th Sep | --:-- | FL3 | Brighton and Hove Albion | A | L | 0-1 | 5705 | |
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| Sat 2nd Oct | --:-- | FL3 | Rotherham United | H | L | 0-2 | 3331 | |
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| Sat 9th Oct | --:-- | FL3 | Southend United | H | W | 2-1 | 3118 | |
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| Sat 16th Oct | --:-- | FL3 | Darlington | A | L | 0-1 | 4802 | |
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| Tue 19th Oct | --:-- | FL3 | Chester City | A | L | 1-2 | 1705 | |
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| Sat 23rd Oct | --:-- | FL3 | Brighton and Hove Albion | H | D | 0-0 | 4050 | |
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| Sat 30th Oct | --:-- | FAC | Gillingham | H | D | 1-1 | |
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| Tue 2nd Nov | --:-- | FL3 | Halifax Town | A | D | 1-1 | 1956 | |
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| Sat 6th Nov | --:-- | FL3 | Carlisle United | H | W | 3-1 | 3118 | |
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| Tue 9th Nov | --:-- | FAC | Gillingham | A | L | 2-3 | |
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| Fri 12th Nov | --:-- | FL3 | Northampton Town | A | L | 2-3 | 5837 | |
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| Tue 16th Nov | --:-- | FL3 | Swansea City | A | D | 0-0 | 4299 | |
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| Tue 23rd Nov | --:-- | FL3 | Plymouth Argyle | H | W | 2-0 | 5140 | |
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| Sat 27th Nov | --:-- | FL3 | Leyton Orient | H | W | 2-0 | 3604 | |
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| Sat 4th Dec | --:-- | FL3 | Rochdale | A | D | 0-0 | 2245 | |
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| Tue 7th Dec | --:-- | AMC | Southend United | A | W | 1-0 | |
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| Sat 11th Dec | --:-- | FL3 | Macclesfield Town | H | D | 1-1 | 3107 | |
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| Sun 26th Dec | --:-- | FL3 | Exeter City | H | W | 3-1 | 5012 | |
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| Tue 28th Dec | --:-- | FL3 | York City | A | W | 2-1 | 2936 | |
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| Mon 3rd Jan | --:-- | FL3 | Lincoln City | H | L | 0-2 | 4012 | |
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| Sat 8th Jan | --:-- | FL3 | Macclesfield Town | A | W | 2-1 | 3221 | |
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| Wed 12th Jan | --:-- | AMC | Bristol City | A | L | 1-3 | |
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| Sat 15th Jan | --:-- | FL3 | Mansfield Town | H | W | 1-0 | 3150 | |
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| Sat 22nd Jan | --:-- | FL3 | Hull City | A | D | 1-1 | 4691 | |
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| Sat 29th Jan | --:-- | FL3 | Hartlepool United | H | W | 2-1 | 3630 | |
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| Sat 5th Feb | --:-- | FL3 | Barnet | A | L | 2-3 | 2727 | |
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| Sun 13th Feb | --:-- | FL3 | Swansea City | H | D | 0-0 | 4220 | |
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| Sat 19th Feb | --:-- | FL3 | Leyton Orient | A | L | 0-1 | 4884 | |
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| Sat 26th Feb | --:-- | FL3 | Peterborough United | H | W | 2-1 | 4250 | |
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| Sat 4th Mar | --:-- | FL3 | Shrewsbury Town | A | W | 2-0 | 2876 | |
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| Sat 11th Mar | --:-- | FL3 | Halifax Town | H | W | 3-0 | 3478 | |
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| Tue 14th Mar | --:-- | FL3 | Torquay United | A | D | 1-1 | 2378 | |
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| Sat 18th Mar | --:-- | FL3 | Plymouth Argyle | A | L | 0-1 | 4392 | |
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| Tue 21st Mar | --:-- | FL3 | Northampton Town | H | W | 2-1 | 4515 | |
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| Sat 25th Mar | --:-- | FL3 | Exeter City | A | W | 2-1 | 3007 | |
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| Sat 1st Apr | --:-- | FL3 | Torquay United | H | W | 2-0 | 5128 | |
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| Tue 4th Apr | --:-- | FL3 | Carlisle United | A | D | 1-1 | 2388 | |
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| Sat 8th Apr | --:-- | FL3 | Lincoln City | A | W | 2-1 | 3133 | |
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| Sat 15th Apr | --:-- | FL3 | York City | H | L | 0-1 | 4722 | |
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| Sat 22nd Apr | --:-- | FL3 | Darlington | H | D | 0-0 | 5059 | |
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| Mon 24th Apr | --:-- | FL3 | Rotherham United | A | L | 0-2 | 5447 | |
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| Sat 29th Apr | --:-- | FL3 | Chester City | H | W | 1-0 | 5391 | |
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| Sat 6th May | --:-- | FL3 | Southend United | A | L | 1-2 | 4977 | |