York City
1999-2000
[squad stats] [appearance chart]
| Date | K.O. | Comp | Opponents | Ven | Res | Att | ||||
| Sat 7th Aug | --:-- | FL3 | Swansea City | H | W | 1-0 | 3036 |  |
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| Tue 10th Aug | --:-- | LC | Wigan Athletic | H | L | 0-1 | |
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| Sat 14th Aug | --:-- | FL3 | Torquay United | A | D | 0-0 | 3005 | |
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| Sat 21st Aug | --:-- | FL3 | Rochdale | H | L | 0-3 | 3034 | |
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| Tue 24th Aug | --:-- | LC | Wigan Athletic | A | L | 1-2 | |
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| Sat 28th Aug | --:-- | FL3 | Barnet | A | L | 3-6 | 1896 | |
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| Mon 30th Aug | --:-- | FL3 | Northampton Town | H | L | 0-1 | 2597 | |
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| Sat 4th Sep | --:-- | FL3 | Rotherham United | A | L | 0-1 | 3171 | |
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| Sat 11th Sep | --:-- | FL3 | Peterborough United | H | D | 0-0 | 2832 | |
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| Sat 18th Sep | --:-- | FL3 | Exeter City | A | L | 1-2 | 2904 | |
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| Sat 25th Sep | --:-- | FL3 | Hull City | A | D | 1-1 | 8293 | |
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| Sat 2nd Oct | --:-- | FL3 | Chester City | H | D | 2-2 | 2452 | |
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| Sat 9th Oct | --:-- | FL3 | Leyton Orient | H | W | 2-1 | 2320 | |
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| Sat 16th Oct | --:-- | FL3 | Brighton and Hove Albion | A | W | 1-0 | 5862 | |
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| Tue 19th Oct | --:-- | FL3 | Halifax Town | A | W | 2-0 | 2963 | |
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| Sat 23rd Oct | --:-- | FL3 | Hull City | H | D | 1-1 | 5109 | |
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| Sat 30th Oct | --:-- | FAC | Hereford United | A | L | 0-1 | |
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| Tue 2nd Nov | --:-- | FL3 | Carlisle United | A | W | 1-0 | 2512 | |
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| Sat 6th Nov | --:-- | FL3 | Macclesfield Town | H | L | 0-2 | 2469 | |
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| Fri 12th Nov | --:-- | FL3 | Lincoln City | A | L | 2-4 | 2956 | |
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| Tue 23rd Nov | --:-- | FL3 | Shrewsbury Town | H | W | 1-0 | 1857 | |
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| Sat 27th Nov | --:-- | FL3 | Plymouth Argyle | H | D | 0-0 | 2745 | |
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| Sat 4th Dec | --:-- | FL3 | Swansea City | A | L | 0-1 | 3812 | |
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| Tue 7th Dec | --:-- | AMC | Hull City | H | L | 0-1 | |
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| Fri 17th Dec | --:-- | FL3 | Southend United | H | D | 2-2 | 2233 | |
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| Sun 26th Dec | --:-- | FL3 | Hartlepool United | A | L | 1-2 | 4668 | |
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| Tue 28th Dec | --:-- | FL3 | Cheltenham Town | H | L | 1-2 | 2936 | |
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| Sat 8th Jan | --:-- | FL3 | Mansfield Town | H | L | 0-1 | 2458 | |
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| Sat 15th Jan | --:-- | FL3 | Torquay United | H | D | 2-2 | 2427 | |
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| Tue 18th Jan | --:-- | FL3 | Darlington | A | D | 2-2 | 5704 | |
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| Sat 22nd Jan | --:-- | FL3 | Rochdale | A | L | 1-2 | 2580 | |
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| Sat 29th Jan | --:-- | FL3 | Barnet | H | W | 1-0 | 2497 | |
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| Sat 5th Feb | --:-- | FL3 | Northampton Town | A | L | 0-3 | 4958 | |
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| Tue 8th Feb | --:-- | FL3 | Mansfield Town | A | L | 0-1 | 2571 | |
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| Sat 12th Feb | --:-- | FL3 | Rotherham United | H | L | 1-2 | 4531 | |
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| Sat 19th Feb | --:-- | FL3 | Plymouth Argyle | A | L | 0-2 | 4343 | |
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| Sat 26th Feb | --:-- | FL3 | Exeter City | H | D | 0-0 | 3066 | |
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| Sat 4th Mar | --:-- | FL3 | Peterborough United | A | L | 0-2 | 5578 | |
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| Tue 7th Mar | --:-- | FL3 | Macclesfield Town | A | D | 1-1 | 1581 | |
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| Sat 11th Mar | --:-- | FL3 | Carlisle United | H | D | 1-1 | 2976 | |
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| Sat 18th Mar | --:-- | FL3 | Shrewsbury Town | A | W | 1-0 | 2149 | |
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| Tue 21st Mar | --:-- | FL3 | Lincoln City | H | W | 2-0 | 2449 | |
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| Sat 25th Mar | --:-- | FL3 | Hartlepool United | H | W | 2-1 | 4079 | |
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| Sat 1st Apr | --:-- | FL3 | Southend United | A | D | 0-0 | 3364 | |
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| Sat 8th Apr | --:-- | FL3 | Darlington | H | D | 0-0 | 5308 | |
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| Sat 15th Apr | --:-- | FL3 | Cheltenham Town | A | W | 1-0 | 4722 | |
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| Sat 22nd Apr | --:-- | FL3 | Brighton and Hove Albion | H | D | 0-0 | 3619 | |
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| Mon 24th Apr | --:-- | FL3 | Chester City | A | L | 0-2 | 3503 | |
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| Sat 29th Apr | --:-- | FL3 | Halifax Town | H | W | 2-0 | 3079 | |
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| Sat 6th May | --:-- | FL3 | Leyton Orient | A | D | 0-0 | 4594 | |