- 2022-10-19 4y Tottenham Hotspur FC 3 at Middlesbrough 0 Heurelho da Silva Gomes ENG-TOXG 90min
- 2020-01-15 6y Middlesbrough 1 at Tottenham Hotspur FC 2 Erik Lamela ENG-TOXG 90min 1g
- 2020-01-05 6y Tottenham Hotspur FC 1 at Middlesbrough 1
- 2017-02-04 9y Middlesbrough 0 at Tottenham Hotspur FC 1 Harry Kane ENG-TOXG 90min 1g
- 2016-09-24 10y Tottenham Hotspur FC 2 at Middlesbrough 1 Heung-Min Son ENG-TOXG 90min 2g
- 2009-03-04 17y Middlesbrough 0 at Tottenham Hotspur FC 4 Robbie Keane ENG-TOXG 90min 1g
- 2008-04-12 18y Middlesbrough 1 at Tottenham Hotspur FC 1
- 2007-11-03 18y Tottenham Hotspur FC 1 at Middlesbrough 1
- 2007-09-27 19y Middlesbrough 0 at Tottenham Hotspur FC 2
- 2007-04-28 19y Tottenham Hotspur FC 3 at Middlesbrough 2 Robbie Keane ENG-TOXG 90min 2g
- 2006-12-05 19y Middlesbrough 1 at Tottenham Hotspur FC 2 Dimitar Ivanov Berbatov ENG-TOXG 90min 1g
- 2005-12-18 20y Tottenham Hotspur FC 3 at Middlesbrough 3
- 2005-08-20 21y Middlesbrough 0 at Tottenham Hotspur FC 2 Ahmed Hossam Hussein Abdelhamid ENG-TOXG 90min 1g
- 2005-05-07 21y Tottenham Hotspur FC 0 at Middlesbrough 1 George Boateng ENG-MIRM 90min 1g
- 2004-11-28 21y Middlesbrough 0 at Tottenham Hotspur FC 2 Jermain Colin Defoe ENG-TOXG 90min 1g yc
- 2003-10-26 22y Middlesbrough 0 at Tottenham Hotspur FC 0
- 2003-05-02 23y Tottenham Hotspur FC 1 at Middlesbrough 5 Oswaldo Giroldo Júnior ENG-MIRM 90min 1g
- 2002-09-27 24y Middlesbrough 3 at Tottenham Hotspur FC 0
- 2002-03-29 24y Tottenham Hotspur FC 1 at Middlesbrough 1
- 2001-10-26 24y Middlesbrough 1 at Tottenham Hotspur FC 2
- 2000-12-22 25y Middlesbrough 0 at Tottenham Hotspur FC 0
- 2000-08-21 26y Tottenham Hotspur FC 1 at Middlesbrough 1
- 2000-04-02 26y Middlesbrough 3 at Tottenham Hotspur FC 2
- 1999-12-17 26y Tottenham Hotspur FC 1 at Middlesbrough 2
- 1999-02-19 27y Tottenham Hotspur FC 0 at Middlesbrough 0
- 1998-09-12 28y Middlesbrough 3 at Tottenham Hotspur FC 0
- 1997-04-23 29y Middlesbrough 0 at Tottenham Hotspur FC 1
- 1996-10-18 30y Tottenham Hotspur FC 3 at Middlesbrough 0
- 1996-04-07 30y Middlesbrough 1 at Tottenham Hotspur FC 1
- 1995-11-20 30y Tottenham Hotspur FC 1 at Middlesbrough 0
- 1993-04-19 33y Tottenham Hotspur FC 0 at Middlesbrough 3
- 1992-10-16 34y Middlesbrough 2 at Tottenham Hotspur FC 2
- 1989-01-21 37y Tottenham Hotspur FC 2 at Middlesbrough 2
- 1988-09-24 38y Middlesbrough 2 at Tottenham Hotspur FC 3
- 1982-01-27 44y Middlesbrough 0 at Tottenham Hotspur FC 1
- 1980-12-20 45y Tottenham Hotspur FC 1 at Middlesbrough 4
- 1980-10-11 46y Middlesbrough 2 at Tottenham Hotspur FC 3
- 1979-11-03 46y Tottenham Hotspur FC 0 at Middlesbrough 0
- 1979-08-18 47y Middlesbrough 3 at Tottenham Hotspur FC 1
- 1979-04-07 47y Middlesbrough 2 at Tottenham Hotspur FC 1
- 1979-03-31 47y Tottenham Hotspur FC 0 at Middlesbrough 1
- 1975-12-20 50y Tottenham Hotspur FC 0 at Middlesbrough 1
- 1975-08-16 51y Middlesbrough 0 at Tottenham Hotspur FC 1
- 1975-03-15 51y Tottenham Hotspur FC 0 at Middlesbrough 3
- 1974-09-28 52y Middlesbrough 2 at Tottenham Hotspur FC 1
- 1954-01-02 72y Tottenham Hotspur FC 0 at Middlesbrough 3
- 1952-12-27 73y Tottenham Hotspur FC 4 at Middlesbrough 0
- 1952-12-25 73y Middlesbrough 1 at Tottenham Hotspur FC 7
- 1951-12-15 74y Middlesbrough 1 at Tottenham Hotspur FC 3
- 1951-08-18 75y Tottenham Hotspur FC 1 at Middlesbrough 2