| League Cup | 26.09.00 | Macclesfield Town | - | Middlesbrough FC | 1:3 | ||||
| Pr. League | 18.11.00 | Middlesbrough FC | - | Leicester City | 0:3 | ||||
| Pr. League | 03.02.01 | Middlesbrough FC | - | Manchester City | 1:1 | ||||
| Pr. League | 29.09.01 | Middlesbrough FC | - | Southampton FC | 1:3 |  |
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| League Cup | 10.10.01 | Blackburn Rovers | - | Middlesbrough FC | 2:1 n.V. | ||||
| FA Cup | 10.03.02 | Middlesbrough FC | - | Everton FC | 3:0 |
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