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