| League Cup | 27/10/98 | Middlesbrough FC | - | Everton FC | 2:3 aet | ||||
| Pr. League | 14/04/99 | Middlesbrough FC | - | Chelsea FC | 0:0 | ||||
| Pr. League | 07/08/99 | Middlesbrough FC | - | Bradford City | 0:1 |  |
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| Pr. League | 20/11/99 | Arsenal FC | - | Middlesbrough FC | 5:1 | ||||
| Pr. League | 15/04/00 | Coventry City | - | Middlesbrough FC | 2:1 | ||||
| Pr. League | 24/02/01 | Middlesbrough FC | - | Southampton FC | 0:1 | ||||
| Pr. League | 17/09/01 | Leicester City | - | Middlesbrough FC | 1:2 | ||||
| Pr. League | 03/11/01 | Middlesbrough FC | - | Derby County | 5:1 |  |
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| Pr. League | 09/02/02 | Middlesbrough FC | - | Leeds United | 2:2 | ||||
| Pr. League | 20/04/02 | Middlesbrough FC | - | Blackburn Rovers | 1:3 | |
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| Pr. League | 20/10/02 | Charlton Athletic | - | Middlesbrough FC | 1:0 |
England