| Pr. League | 28/12/96 | Coventry City | - | Middlesbrough FC | 3:0 | ||||
| Pr. League | 15/03/97 | Leicester City | - | Middlesbrough FC | 1:3 |  |
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| FA Cup | 17/05/97 | Chelsea FC | - | Middlesbrough FC | 2:0 | ||||
| League Cup | 17/11/97 | Middlesbrough FC | - | Bolton Wanderers | 2:1 aet |  |
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| Pr. League | 24/10/98 | Wimbledon FC | - | Middlesbrough FC | 2:2 | ||||
| Pr. League | 16/01/99 | Leeds United | - | Middlesbrough FC | 2:0 | ||||
| Pr. League | 10/08/99 | Derby County | - | Arsenal FC | 1:2 |
Denmark