1. Round | 19/08/2000 | Coventry City | - | Middlesbrough FC | 1:3 | ||||
2. Round | 22/08/2000 | Middlesbrough FC | - | Tottenham Hotspur | 1:1 | ||||
3. Round | 26/08/2000 | Middlesbrough FC | - | Leeds United | 1:2 | ||||
6. Round | 17/09/2000 | Manchester City | - | Middlesbrough FC | 1:1 | ![]() |
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7. Round | 23/09/2000 | Middlesbrough FC | - | Aston Villa | 1:1 | ||||
8. Round | 30/09/2000 | Southampton FC | - | Middlesbrough FC | 1:3 | ![]() |
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17. Round | 09/12/2000 | Sunderland AFC | - | Middlesbrough FC | 1:0 | ![]() |
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18. Round | 16/12/2000 | Middlesbrough FC | - | Chelsea FC | 1:0 | ||||
19. Round | 23/12/2000 | Tottenham Hotspur | - | Middlesbrough FC | 0:0 | ![]() |
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20. Round | 26/12/2000 | Middlesbrough FC | - | Liverpool FC | 1:0 | ||||
21. Round | 30/12/2000 | Middlesbrough FC | - | Coventry City | 1:1 | ||||
23. Round | 13/01/2001 | Middlesbrough FC | - | Derby County | 4:0 | ||||
26. Round | 03/02/2001 | Middlesbrough FC | - | Manchester City | 1:1 | ![]() |
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27. Round | 10/02/2001 | Aston Villa | - | Middlesbrough FC | 1:1 | ||||
31. Round | 31/03/2001 | Chelsea FC | - | Middlesbrough FC | 2:1 |