Chelsea
1999-2000
[squad stats] [appearance chart]
| Date | K.O. | Comp | Opponents | Ven | Res | Att | ||||
| Sat 7th Aug | --:-- | Prem | Sunderland | H | W | 4-0 | 34831 |  |
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| Sat 14th Aug | --:-- | Prem | Leicester City | A | D | 2-2 | 21068 | |
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| Sat 21st Aug | --:-- | Prem | Aston Villa | H | W | 1-0 | 35071 | |
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| Sat 28th Aug | --:-- | Prem | Wimbledon | A | W | 1-0 | 22167 | |
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| Sat 11th Sep | --:-- | Prem | Newcastle United | H | W | 1-0 | 35092 | |
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| Sat 18th Sep | --:-- | Prem | Watford | A | L | 0-1 | 21244 | |
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| Sat 25th Sep | --:-- | Prem | Middlesbrough | A | W | 1-0 | 34183 | |
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| Sun 3rd Oct | --:-- | Prem | Manchester United | H | W | 5-0 | 34909 | |
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| Wed 13th Oct | --:-- | LC | Huddersfield Town | H | L | 0-1 | |
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| Sat 16th Oct | --:-- | Prem | Liverpool | A | L | 0-1 | 44826 | |
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| Sat 23rd Oct | --:-- | Prem | Arsenal | H | L | 2-3 | 34958 | |
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| Sat 30th Oct | --:-- | Prem | Derby County | A | L | 1-3 | 28614 | |
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| Sun 7th Nov | --:-- | Prem | West Ham United | H | D | 0-0 | 34935 | |
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| Sat 20th Nov | --:-- | Prem | Everton | A | D | 1-1 | 38225 | |
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| Sun 28th Nov | --:-- | Prem | Bradford City | H | W | 1-0 | 31591 | |
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| Sat 4th Dec | --:-- | Prem | Sunderland | A | L | 1-4 | 41377 | |
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| Sat 11th Dec | --:-- | FAC | Hull City | A | W | 6-1 | |
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| Sun 19th Dec | --:-- | Prem | Leeds United | H | L | 0-2 | 35106 | |
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| Sun 26th Dec | --:-- | Prem | Southampton | A | W | 2-1 | 15232 | |
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| Wed 29th Dec | --:-- | Prem | Sheffield Wednesday | H | W | 3-0 | 32938 | |
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| Tue 4th Jan | --:-- | Prem | Coventry City | A | D | 2-2 | 20164 | |
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| Sat 8th Jan | --:-- | Prem | Bradford City | A | D | 1-1 | 18276 | |
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| Wed 12th Jan | --:-- | Prem | Tottenham Hotspur | H | W | 1-0 | 34969 | |
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| Sat 15th Jan | --:-- | Prem | Leicester City | H | D | 1-1 | 35063 | |
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| Wed 19th Jan | --:-- | FAC | Nottingham Forest | H | W | 2-0 | |
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| Sat 22nd Jan | --:-- | Prem | Aston Villa | A | D | 0-0 | 33704 | |
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| Sun 30th Jan | --:-- | FAC | Leicester City | H | W | 2-1 | |
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| Sat 5th Feb | --:-- | Prem | Tottenham Hotspur | A | W | 1-0 | 36041 | |
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| Sat 12th Feb | --:-- | Prem | Wimbledon | H | W | 3-1 | 34826 | |
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| Sun 20th Feb | --:-- | FAC | Gillingham | H | W | 5-0 | |
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| Sat 26th Feb | --:-- | Prem | Watford | H | W | 2-1 | 34928 | |
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| Sat 4th Mar | --:-- | Prem | Newcastle United | A | W | 1-0 | 36448 | |
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| Sat 11th Mar | --:-- | Prem | Everton | H | D | 1-1 | 35113 | |
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| Sat 18th Mar | --:-- | Prem | West Ham United | A | D | 0-0 | 26041 | |
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| Sat 25th Mar | --:-- | Prem | Southampton | H | D | 1-1 | 34956 | |
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| Sat 1st Apr | --:-- | Prem | Leeds United | A | W | 1-0 | 40162 | |
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| Sun 9th Apr | --:-- | FAC | Newcastle United | A | W | 2-1 | |
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| Wed 12th Apr | --:-- | Prem | Coventry City | H | W | 2-1 | 32316 | |
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| Sat 15th Apr | --:-- | Prem | Sheffield Wednesday | A | L | 0-1 | 21743 | |
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| Sat 22nd Apr | --:-- | Prem | Middlesbrough | H | D | 1-1 | 34467 | |
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| Mon 24th Apr | --:-- | Prem | Manchester United | A | L | 2-3 | 61593 | |
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| Sat 29th Apr | --:-- | Prem | Liverpool | H | W | 2-0 | 34957 | |
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| Sat 6th May | --:-- | Prem | Arsenal | A | L | 1-2 | 38119 | |
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| Sun 14th May | --:-- | Prem | Derby County | H | W | 4-0 | 35084 | |
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| Sat 20th May | --:-- | FAC | Aston Villa | - | W | 1-0 | 78217 |  |