| League Cup | 28.10.98 | Middlesbrough | - | Everton | 2:3 pró. | ||||
| Pr. League | 14.04.99 | Middlesbrough | - | Chelsea | 0:0 |  |
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| Pr. League | 07.08.99 | Middlesbrough | - | Bradford City | 0:1 | ||||
| Pr. League | 20.11.99 | Arsenal | - | Middlesbrough | 5:1 | |
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| Pr. League | 15.04.00 | Coventry City | - | Middlesbrough | 2:1 | ||||
| Pr. League | 28.10.00 | Ipswich Town | - | Middlesbrough | 2:1 | ||||
| Pr. League | 24.02.01 | Middlesbrough | - | Southampton | 0:1 | ||||
| Pr. League | 09.02.02 | Middlesbrough | - | Leeds United | 2:2 | ||||
| Pr. League | 20.04.02 | Middlesbrough | - | Blackburn Rovers | 1:3 | |
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