| At Tottenham (33) | At Middlesbrough (33) | Overall (66 matches) | ||||||||
| Results | Total | % | Results | Total | % | Results | Total | % | ||
| Tottenham | 17 | 51.52 | Middlesbrough | 19 | 57.58 | Tottenham | 22 | 33.33 | ||
| Middlesbrough | 9 | 27.27 | Tottenham | 5 | 15.15 | Middlesbrough | 28 | 42.42 | ||
| Draws | 7 | 21.21 | Draws | 9 | 27.27 | Draws | 16 | 24.24 | ||
| Goals | Total | Av.pg | Goals | Total | Av.pg | Goals | Total | Av.pg | ||
| Tottenham | 72 | 2.18 | Middlesbrough | 62 | 1.88 | Tottenham | 104 | 1.58 | ||
| Middlesbrough | 55 | 1.67 | Tottenham | 32 | 0.97 | Middlesbrough | 117 | 1.77 | ||
| Records | |||||
| Highest Aggregate | 12 | Middlesbrough | 7 - 5 | Tottenham | 1914/1915 |
| Highest Tottenham score: | 7 | Tottenham | 7 - 1 | Middlesbrough | 1952/1953 |
| Highest Middlesbrough score: | 7 | Middlesbrough | 7 - 5 | Tottenham | 1914/1915 |
| Season | Date | Home | Score | Away | Competition |
| 2001/2002 | Sat 30 Mar | Middlesbrough | 1 - 1 | Tottenham | Premiership |
| Sat 27 Oct | Tottenham | 2 - 1 | Middlesbrough | Premiership | |
| 2000/2001 | Sat 23 Dec | Tottenham | 0 - 0 | Middlesbrough | Premiership |
| Tue 22 Aug | Middlesbrough | 1 - 1 | Tottenham | Premiership | |
| 1999/2000 | Mon 03 Apr | Tottenham | 2 - 3 | Middlesbrough | Premiership |
| Sat 18 Dec | Middlesbrough | 2 - 1 | Tottenham | Premiership | |
| 1998/1999 | Sat 20 Feb | Middlesbrough | 0 - 0 | Tottenham | Premiership |
| Sun 13 Sep | Tottenham | 0 - 3 | Middlesbrough | Premiership | |
| 1996/1997 | Thu 24 Apr | Tottenham | 1 - 0 | Middlesbrough | Premiership |
| Sat 19 Oct | Middlesbrough | 0 - 3 | Tottenham | Premiership | |
| 1995/1996 | Mon 08 Apr | Tottenham | 1 - 1 | Middlesbrough | Premiership |
| Tue 21 Nov | Middlesbrough | 0 - 1 | Tottenham | Premiership | |
| 1992/1993 | Tue 20 Apr | Middlesbrough | 3 - 0 | Tottenham | Premiership |
| Sat 17 Oct | Tottenham | 2 - 2 | Middlesbrough | Premiership | |
| 1988/1989 | Sat 21 Jan | Middlesbrough | 2 - 2 | Tottenham | First Division |
| Sat 24 Sep | Tottenham | 3 - 2 | Middlesbrough | First Division | |
| 1981/1982 | Wed 27 Jan | Tottenham | 1 - 0 | Middlesbrough | First Division |
| Sat 29 Aug | Middlesbrough | 1 - 3 | Tottenham | First Division | |
| 1980/1981 | Sat 20 Dec | Middlesbrough | 4 - 1 | Tottenham | First Division |
| Sat 11 Oct | Tottenham | 3 - 2 | Middlesbrough | First Division | |
| 1979/1980 | Sat 03 Nov | Middlesbrough | 0 - 0 | Tottenham | First Division |
| Sat 18 Aug | Tottenham | 1 - 3 | Middlesbrough | First Division | |
| 1978/1979 | Sat 07 Apr | Tottenham | 1 - 2 | Middlesbrough | First Division |
| Sat 31 Mar | Middlesbrough | 1 - 0 | Tottenham | First Division | |
| 1976/1977 | Sat 05 Feb | Middlesbrough | 2 - 0 | Tottenham | First Division |
| Sat 28 Aug | Tottenham | 0 - 0 | Middlesbrough | First Division | |
| 1975/1976 | Sat 20 Dec | Middlesbrough | 1 - 0 | Tottenham | First Division |
| Sat 16 Aug | Tottenham | 1 - 0 | Middlesbrough | First Division | |
| 1974/1975 | Sat 15 Mar | Middlesbrough | 3 - 0 | Tottenham | First Division |
| Sat 28 Sep | Tottenham | 1 - 2 | Middlesbrough | First Division | |
| 1953/1954 | Sat 02 Jan | Middlesbrough | 3 - 0 | Tottenham | First Division |
| Sat 29 Aug | Tottenham | 4 - 1 | Middlesbrough | First Division | |
| 1952/1953 | Sat 27 Dec | Middlesbrough | 0 - 4 | Tottenham | First Division |
| Thu 25 Dec | Tottenham | 7 - 1 | Middlesbrough | First Division | |
| 1951/1952 | Sat 15 Dec | Tottenham | 3 - 1 | Middlesbrough | First Division |
| Sat 18 Aug | Middlesbrough | 2 - 1 | Tottenham | First Division | |
| 1950/1951 | Sat 21 Apr | Middlesbrough | 1 - 1 | Tottenham | First Division |
| Sat 02 Dec | Tottenham | 3 - 3 | Middlesbrough | First Division | |
| 1934/1935 | Sat 23 Mar | Middlesbrough | 3 - 1 | Tottenham | First Division |
| Sat 10 Nov | Tottenham | 3 - 1 | Middlesbrough | First Division | |
| 1933/1934 | Sat 10 Mar | Middlesbrough | 1 - 1 | Tottenham | First Division |
| Sat 28 Oct | Tottenham | 2 - 0 | Middlesbrough | First Division | |
| 1928/1929 | Tue 01 Jan | Middlesbrough | 3 - 0 | Tottenham | Second Division |
| Mon 27 Aug | Tottenham | 2 - 5 | Middlesbrough | Second Division | |
| 1927/1928 | Mon 12 Sep | Tottenham | 4 - 2 | Middlesbrough | First Division |
| Wed 31 Aug | Middlesbrough | 3 - 1 | Tottenham | First Division | |
| 1923/1924 | Sat 15 Sep | Middlesbrough | 0 - 1 | Tottenham | First Division |
| Sat 08 Sep | Tottenham | 2 - 1 | Middlesbrough | First Division | |
| 1922/1923 | Sat 06 Jan | Tottenham | 2 - 0 | Middlesbrough | First Division |
| Sat 30 Dec | Middlesbrough | 2 - 0 | Tottenham | First Division | |
| 1921/1922 | Sat 17 Sep | Middlesbrough | 0 - 0 | Tottenham | First Division |
| Sat 10 Sep | Tottenham | 2 - 4 | Middlesbrough | First Division | |
| 1920/1921 | Sat 07 May | Tottenham | 2 - 2 | Middlesbrough | First Division |
| Mon 02 May | Middlesbrough | 1 - 0 | Tottenham | First Division | |
| 1914/1915 | Sat 13 Feb | Middlesbrough | 7 - 5 | Tottenham | First Division |
| Sat 10 Oct | Tottenham | 3 - 3 | Middlesbrough | First Division | |
| 1913/1914 | Mon 13 Apr | Middlesbrough | 6 - 0 | Tottenham | First Division |
| Fri 26 Dec | Tottenham | 0 - 1 | Middlesbrough | First Division | |
| 1912/1913 | Sat 08 Feb | Tottenham | 5 - 3 | Middlesbrough | First Division |
| Sat 05 Oct | Middlesbrough | 1 - 1 | Tottenham | First Division | |
| 1911/1912 | Sat 17 Feb | Tottenham | 2 - 1 | Middlesbrough | First Division |
| Sat 14 Oct | Middlesbrough | 2 - 0 | Tottenham | First Division | |
| 1910/1911 | Mon 13 Feb | Tottenham | 6 - 2 | Middlesbrough | First Division |
| Sat 01 Oct | Middlesbrough | 2 - 0 | Tottenham | First Division | |
| 1909/1910 | Sat 26 Feb | Middlesbrough | 4 - 3 | Tottenham | First Division |
| Sat 16 Oct | Tottenham | 1 - 3 | Middlesbrough | First Division | |