| League Cup | 22.09.98 | Wycombe Wanderers | - | Middlesbrough FC | 1:1 |  |
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| Pr. League | 29.11.98 | Arsenal FC | - | Middlesbrough FC | 1:1 | ||||
| FA Cup | 03.01.99 | Manchester United | - | Middlesbrough FC | 3:1 | ||||
| Pr. League | 09.05.99 | Middlesbrough FC | - | Manchester United | 0:1 | ||||
| Pr. League | 06.11.99 | Middlesbrough FC | - | Sunderland AFC | 1:1 | |
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| Pr. League | 19.02.00 | Middlesbrough FC | - | Coventry City | 2:0 | |
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| Pr. League | 26.08.00 | Middlesbrough FC | - | Leeds United | 1:2 | ||||
| FA Cup | 08.01.01 | Bradford City | - | Middlesbrough FC | 0:1 | |
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| Pr. League | 31.01.01 | Everton FC | - | Middlesbrough FC | 2:2 | |
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| Pr. League | 17.03.01 | Newcastle United | - | Middlesbrough FC | 1:2 | ||||
| Pr. League | 05.05.01 | Bradford City | - | Middlesbrough FC | 1:1 |  |
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| Pr. League | 18.08.01 | Middlesbrough FC | - | Arsenal FC | 0:4 |
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