Tottenham Hotspur
1999-2000
[squad stats] [appearance chart]
| Date | K.O. | Comp | Opponents | Ven | Res | Att | ||||
| Sat 7th Aug | --:-- | Prem | West Ham United | A | L | 0-1 | 26010 |  |
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| Mon 9th Aug | --:-- | Prem | Newcastle United | H | W | 3-1 | 28701 | |
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| Sat 14th Aug | --:-- | Prem | Everton | H | W | 3-2 | 34539 | |
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| Sat 21st Aug | --:-- | Prem | Sheffield Wednesday | A | W | 2-1 | 24027 | |
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| Sat 28th Aug | --:-- | Prem | Leeds United | H | L | 1-2 | 36012 | |
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| Sun 12th Sep | --:-- | Prem | Bradford City | A | D | 1-1 | 18143 | |
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| Sun 19th Sep | --:-- | Prem | Coventry City | H | W | 3-2 | 35224 | |
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| Sun 26th Sep | --:-- | Prem | Wimbledon | A | D | 1-1 | 17368 | |
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| Sun 3rd Oct | --:-- | Prem | Leicester City | H | L | 2-3 | 35591 | |
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| Wed 13th Oct | --:-- | LC | Crewe Alexandra | H | W | 3-1 | |
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| Sat 16th Oct | --:-- | Prem | Derby County | A | W | 1-0 | 29815 | |
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| Sat 23rd Oct | --:-- | Prem | Manchester United | H | W | 3-1 | 36072 | |
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| Sun 31st Oct | --:-- | Prem | Sunderland | A | L | 1-2 | 41904 | |
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| Sun 7th Nov | --:-- | Prem | Arsenal | H | W | 2-1 | 36085 | |
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| Sat 20th Nov | --:-- | Prem | Southampton | A | W | 1-0 | 15248 | |
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| Sun 28th Nov | --:-- | Prem | Newcastle United | A | L | 1-2 | 36460 | |
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| Wed 1st Dec | --:-- | LC | Fulham | A | L | 1-3 | |
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| Mon 6th Dec | --:-- | Prem | West Ham United | H | D | 0-0 | 36233 | |
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| Sun 12th Dec | --:-- | FAC | Newcastle United | H | D | 1-1 | |
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| Sat 18th Dec | --:-- | Prem | Middlesbrough | A | L | 1-2 | 33129 | |
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| Wed 22nd Dec | --:-- | FAC | Newcastle United | A | L | 1-6 | |
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| Sun 26th Dec | --:-- | Prem | Watford | H | W | 4-0 | 36089 | |
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| Wed 29th Dec | --:-- | Prem | Aston Villa | A | D | 1-1 | 39217 | |
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| Mon 3rd Jan | --:-- | Prem | Liverpool | H | W | 1-0 | 36044 | |
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| Wed 12th Jan | --:-- | Prem | Chelsea | A | L | 0-1 | 34969 | |
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| Sat 15th Jan | --:-- | Prem | Everton | A | D | 2-2 | 36144 | |
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| Sat 22nd Jan | --:-- | Prem | Sheffield Wednesday | H | L | 0-1 | 35897 | |
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| Sat 5th Feb | --:-- | Prem | Chelsea | H | L | 0-1 | 36041 | |
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| Sat 12th Feb | --:-- | Prem | Leeds United | A | L | 0-1 | 40127 | |
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| Sat 26th Feb | --:-- | Prem | Coventry City | A | W | 1-0 | 23077 | |
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| Sat 4th Mar | --:-- | Prem | Bradford City | H | D | 1-1 | 35472 | |
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| Sat 11th Mar | --:-- | Prem | Southampton | H | W | 7-2 | 36024 | |
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| Sun 19th Mar | --:-- | Prem | Arsenal | A | L | 1-2 | 38131 | |
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| Sat 25th Mar | --:-- | Prem | Watford | A | D | 1-1 | 20050 | |
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| Mon 3rd Apr | --:-- | Prem | Middlesbrough | H | L | 2-3 | 31796 | |
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| Sun 9th Apr | --:-- | Prem | Liverpool | A | L | 0-2 | 44536 | |
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| Sat 15th Apr | --:-- | Prem | Aston Villa | H | L | 2-4 | 35304 | |
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| Wed 19th Apr | --:-- | Prem | Leicester City | A | W | 1-0 | 19764 | |
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| Sat 22nd Apr | --:-- | Prem | Wimbledon | H | W | 2-0 | 33086 | |
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| Sat 29th Apr | --:-- | Prem | Derby County | H | D | 1-1 | 33044 | |
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| Sat 6th May | --:-- | Prem | Manchester United | A | L | 1-3 | 61629 | |
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| Sun 14th May | --:-- | Prem | Sunderland | H | W | 3-1 | 36070 | |