| FA Cup | 17.05.97 | Chelsea | - | Middlesbrough | 2:0 |  |
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| League Cup | 18.11.97 | Middlesbrough | - | Bolton Wanderers | 2:1 pró. | |
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| Pr. League | 24.10.98 | Wimbledon FC | - | Middlesbrough | 2:2 | ||||
| Pr. League | 16.01.99 | Leeds United | - | Middlesbrough | 2:0 | ||||
| Pr. League | 03.10.99 | Newcastle United | - | Middlesbrough | 2:1 | |
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| FA Cup | 11.12.99 | Wrexham AFC | - | Middlesbrough | 2:1 | ||||
| Pr. League | 17.09.00 | Manchester City | - | Middlesbrough | 1:1 |  |
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| Pr. League | 26.12.00 | Middlesbrough | - | Liverpool | 1:0 |
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