| Championship | 10.01.98 | Charlton Athletic | - | Middlesbrough FC | 3:0 | ||||
| Pr. League | 03.10.98 | Middlesbrough FC | - | Sheffield Wednesday | 4:0 |  |
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| Pr. League | 28.12.98 | Derby County | - | Middlesbrough FC | 2:1 | |
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| Pr. League | 20.02.99 | Middlesbrough FC | - | Tottenham Hotspur | 0:0 |
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