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| Middlesbrough FC |
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2 | : | 3 |
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Tottenham Hotspur | |
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| 2022 • Mar 01 • 20:55 |  |
FA Cup 2021/22 | 5th Round Proper | Middlesbrough FC |
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Tottenham Hotspur | 1 | : | 0 | |
| 2020 • Jan 14 • 21:05 | |
FA Cup 2019/20 | 3rd Round Proper Replays | Tottenham Hotspur |
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Middlesbrough FC | 2 | : | 1 | |
| 2020 • Jan 05 • 15:01 | |
FA Cup 2019/20 | 3rd Round Proper | Middlesbrough FC |
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- |
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Tottenham Hotspur | 1 | : | 1 | |
| 2017 • Feb 04 • 18:30 | |
Premier League 2016/17 | Round #24 | Tottenham Hotspur |
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Middlesbrough FC | 1 | : | 0 | |
| 2016 • Sep 24 • 16:00 | |
Premier League 2016/17 | Round #6 | Middlesbrough FC |
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- |
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Tottenham Hotspur | 1 | : | 2 | |
| 2009 • Mar 04 • 21:00 | |
Premier League 2008/09 | Round #28 | Tottenham Hotspur |
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Middlesbrough FC | 4 | : | 0 | |
| 2008 • Aug 16 • 16:00 | |
Premier League 2008/09 | Round #1 | Middlesbrough FC |
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Tottenham Hotspur | 2 | : | 1 | |
| 2008 • Apr 12 • 16:00 | |
Premier League 2007/08 | Round #34 | Tottenham Hotspur |
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Middlesbrough FC | 1 | : | 1 | |
| 2007 • Nov 03 • 16:00 | |
Premier League 2007/08 | Round #12 | Middlesbrough FC |
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Tottenham Hotspur | 1 | : | 1 | |
| 2007 • Apr 28 • 16:00 | |
Premier League 2006/07 | Round #36 | Middlesbrough FC |
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Tottenham Hotspur | 2 | : | 3 | |
| 2006 • Dec 05 • 21:00 | |
Premier League 2006/07 | Round #15 | Tottenham Hotspur |
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Middlesbrough FC | 2 | : | 1 | |
| 2005 • Dec 18 • 14:30 | |
Premier League 2005/06 | Round #17 | Middlesbrough FC |
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Tottenham Hotspur | 3 | : | 3 | |
| 2005 • Aug 20 • 16:00 | |
Premier League 2005/06 | Round #2 | Tottenham Hotspur |
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Middlesbrough FC | 2 | : | 0 | |
| 13 Matches | ||||||||||||