| Pr. League | 24.10.98 | Wimbledon FC | - | Middlesbrough FC | 2:2 |  |
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| Pr. League | 16.01.99 | Leeds United | - | Middlesbrough FC | 2:0 |  |
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| Pr. League | 11.09.99 | Middlesbrough FC | - | Southampton FC | 3:2 | |
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| FA Cup | 11.12.99 | Wrexham AFC | - | Middlesbrough FC | 2:1 | ||||
| Pr. League | 17.09.00 | Manchester City | - | Middlesbrough FC | 1:1 | |
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| Pr. League | 28.04.01 | Middlesbrough FC | - | Manchester United | 0:2 |
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