Tottenham Hotspur
1998-1999
[squad stats] [appearance chart]
| Date | K.O. | Comp | Opponents | Ven | Res | Att | ||||
| Sat 15th Aug | --:-- | Prem | Wimbledon | A | L | 1-3 |  |
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| Sat 22nd Aug | --:-- | Prem | Sheffield Wednesday | H | L | 0-3 | |
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| Sat 29th Aug | --:-- | Prem | Everton | A | W | 1-0 | |
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| Wed 9th Sep | --:-- | Prem | Blackburn Rovers | H | W | 2-1 | |
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| Sun 13th Sep | --:-- | Prem | Middlesbrough | H | L | 0-3 | |
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| Tue 15th Sep | --:-- | LC | Brentford | A | W | 3-2 | |
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| Sat 19th Sep | --:-- | Prem | Southampton | A | D | 1-1 | |
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| Wed 23rd Sep | --:-- | LC | Brentford | H | W | 3-2 | |
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| Sat 26th Sep | --:-- | Prem | Leeds United | H | D | 3-3 | |
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| Sat 3rd Oct | --:-- | Prem | Derby County | A | W | 1-0 | |
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| Mon 19th Oct | --:-- | Prem | Leicester City | A | L | 1-2 | |
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| Sat 24th Oct | --:-- | Prem | Newcastle United | H | W | 2-0 | |
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| Tue 27th Oct | --:-- | LC | Northampton Town | A | W | 3-1 | |
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| Mon 2nd Nov | --:-- | Prem | Charlton Athletic | H | D | 2-2 | |
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| Sat 7th Nov | --:-- | Prem | Aston Villa | A | L | 2-3 | |
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| Tue 10th Nov | --:-- | LC | Liverpool | A | W | 3-1 | |
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| Sat 14th Nov | --:-- | Prem | Arsenal | A | D | 0-0 | |
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| Sat 21st Nov | --:-- | Prem | Nottingham Forest | H | W | 2-0 | |
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| Sat 28th Nov | --:-- | Prem | West Ham United | A | L | 1-2 | |
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| Wed 2nd Dec | --:-- | LC | Manchester United | H | W | 3-1 | |
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| Sat 5th Dec | --:-- | Prem | Liverpool | H | W | 2-1 | |
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| Sat 12th Dec | --:-- | Prem | Manchester United | H | D | 2-2 | |
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| Sat 19th Dec | --:-- | Prem | Chelsea | A | L | 0-2 | |
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| Sat 26th Dec | --:-- | Prem | Coventry City | A | D | 1-1 | |
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| Mon 28th Dec | --:-- | Prem | Everton | H | W | 4-1 | |
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| Sat 2nd Jan | --:-- | FAC | Watford | H | W | 5-2 | |
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| Sat 9th Jan | --:-- | Prem | Sheffield Wednesday | A | D | 0-0 | |
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| Sat 16th Jan | --:-- | Prem | Wimbledon | H | D | 0-0 | |
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| Sat 23rd Jan | --:-- | FAC | Wimbledon | A | D | 1-1 | |
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| Wed 27th Jan | --:-- | LC | Wimbledon | H | D | 0-0 | |
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| Sat 30th Jan | --:-- | Prem | Blackburn Rovers | A | D | 1-1 | |
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| Tue 2nd Feb | --:-- | FAC | Wimbledon | H | W | 3-0 | |
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| Sat 6th Feb | --:-- | Prem | Coventry City | H | D | 0-0 | |
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| Sat 13th Feb | --:-- | FAC | Leeds United | A | D | 1-1 | |
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| Tue 16th Feb | --:-- | LC | Wimbledon | A | W | 1-0 | |
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| Sat 20th Feb | --:-- | Prem | Middlesbrough | A | D | 0-0 | |
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| Wed 24th Feb | --:-- | FAC | Leeds United | H | W | 2-0 | |
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| Sat 27th Feb | --:-- | Prem | Derby County | H | D | 1-1 | |
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| Tue 2nd Mar | --:-- | Prem | Southampton | H | W | 3-0 | |
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| Wed 10th Mar | --:-- | Prem | Leeds United | A | L | 0-2 | |
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| Sat 13th Mar | --:-- | Prem | Aston Villa | H | W | 1-0 | |
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| Tue 16th Mar | --:-- | FAC | Barnsley | A | W | 1-0 | |
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| Sun 21st Mar | --:-- | LC | Leicester City | A | W | 1-0 | |
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| Sat 3rd Apr | --:-- | Prem | Leicester City | H | L | 0-2 | |
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| Mon 5th Apr | --:-- | Prem | Newcastle United | A | D | 1-1 | |
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| Sun 11th Apr | --:-- | FAC | Newcastle United | A | L | 0-2 | |
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| Sat 17th Apr | --:-- | Prem | Nottingham Forest | A | W | 1-0 | |
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| Tue 20th Apr | --:-- | Prem | Charlton Athletic | A | W | 4-1 | |
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| Sat 24th Apr | --:-- | Prem | West Ham United | H | L | 1-2 | |
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| Sat 1st May | --:-- | Prem | Liverpool | A | L | 2-3 | |
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| Wed 5th May | --:-- | Prem | Arsenal | H | L | 1-3 | |
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| Mon 10th May | --:-- | Prem | Chelsea | H | D | 2-2 | |
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| Sun 16th May | --:-- | Prem | Manchester United | A | L | 1-2 | |