1. Round | 07/08/1999 | Middlesbrough FC | - | Bradford City | 0:1 | ||||
2. Round | 10/08/1999 | Wimbledon FC | - | Middlesbrough FC | 2:3 | ||||
3. Round | 14/08/1999 | Derby County | - | Middlesbrough FC | 1:3 | ![]() |
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4. Round | 21/08/1999 | Middlesbrough FC | - | Liverpool FC | 1:0 | ||||
5. Round | 24/08/1999 | Middlesbrough FC | - | Leicester City | 0:3 | ||||
8. Round | 19/09/1999 | Leeds United | - | Middlesbrough FC | 2:0 | ||||
9. Round | 25/09/1999 | Middlesbrough FC | - | Chelsea FC | 0:1 | ![]() |
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10. Round | 03/10/1999 | Newcastle United | - | Middlesbrough FC | 2:1 | ||||
11. Round | 17/10/1999 | Middlesbrough FC | - | West Ham United | 2:0 | ||||
12. Round | 24/10/1999 | Watford FC | - | Middlesbrough FC | 1:3 | ||||
13. Round | 30/10/1999 | Middlesbrough FC | - | Everton FC | 2:1 | ||||
14. Round | 06/11/1999 | Middlesbrough FC | - | Sunderland AFC | 1:1 | ![]() |
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16. Round | 27/11/1999 | Middlesbrough FC | - | Wimbledon FC | 0:0 | ||||
18. Round | 18/12/1999 | Middlesbrough FC | - | Tottenham Hotspur | 2:1 | ![]() |
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24. Round | 05/02/2000 | Leicester City | - | Middlesbrough FC | 2:1 | ||||
25. Round | 14/02/2000 | Middlesbrough FC | - | Aston Villa | 0:4 |