| Pr. League | 17.04.99 | Coventry City | - | Middlesbrough | 1:2 | ||||
| League Cup | 14.12.99 | Tranmere Rovers | - | Middlesbrough | 2:1 | ||||
| Pr. League | 18.03.00 | Sunderland | - | Middlesbrough | 1:1 |  |
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| Pr. League | 01.01.01 | Leeds United | - | Middlesbrough | 1:1 | |
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| Pr. League | 15.12.01 | Middlesbrough | - | Manchester United | 0:1 |
Colombia