Football League Cup 2023/24, Second Round |
 | 29.08.2023 |  | Fulham | – | Tottenham Hotspur | | 1:1 (1:0),
pen. 5:3 |
| London |
Football League Cup 2021/22, Third round |
| 22.09.2021 | | Wolverhampton Wanderers | – | Tottenham Hotspur | | 2:2 (1:2),
pen. 2:3 |
| Wolverhampton |
Football League Cup 2020/21, Fourth Round |
| 29.09.2020 | | Tottenham Hotspur | – | Chelsea | | 1:1 (0:1),
pen. 5:4 * |
| London |
Football League Cup 2019/20, Third round |
| 24.09.2019 | | Colchester United | – | Tottenham Hotspur | | 0:0,
pen. 4:3 |
| Colchester |
Football League Cup 2018/19, Third round |
| 26.09.2018 | | Tottenham Hotspur | – | Watford | | 2:2 (0:0),
pen. 4:2 |
| Milton Keynes |
Football League Cup 2014/15, Semifinals |
| 28.01.2015 | | Sheffield United | – | Tottenham Hotspur | | 2:2 (0:1) |
| Sheffield |
Football League Cup 2013/14, Fourth Round |
| 30.10.2013 | | Tottenham Hotspur | – | Hull City | | 2:2 aet
(1:0, 1:1),
pen. 8:7 |
| London |
Football League Cup 2011/12, Third round |
| 20.09.2011 | | Stoke City | – | Tottenham Hotspur | | 0:0 aet,
pen. 7:6 |
| Stoke-on-Trent |
Football League Cup 2008/09, Final |
| 01.03.2009 | | Manchester United | – | Tottenham Hotspur | | 0:0 aet,
pen. 4:1 |
| London |
Football League Cup 2007/08, Semifinals |
| 09.01.2008 | | Arsenal | – | Tottenham Hotspur | | 1:1 (0:1) |
| London |
Football League Cup 2006/07, Semifinals |
| 24.01.2007 | | Tottenham Hotspur | – | Arsenal | | 2:2 (2:0) |
| London |
Football League Cup 2004/05, Fifth Round |
| 01.12.2004 | | Tottenham Hotspur | – | Liverpool | | 1:1 aet
(0:0),
pen. 3:4 |
| London |
Football League Cup 2003/04, Fifth Round |
| 17.12.2003 | | Tottenham Hotspur | – | Middlesbrough | | 1:1 aet
(1:0, 1:1),
pen. 4:5 |
| London |
Football League Cup 2000/01, Second round |
| 19.09.2000 | | Brentford | – | Tottenham Hotspur | | 0:0 |
| Brentford |
Football League Cup 1998/99, Semifinals |
| 27.01.1999 | | Tottenham Hotspur | – | Wimbledon | | 0:0 |
| London |
Football League Cup 1996/97, Second round |
| 17.09.1996 | | Preston North End | – | Tottenham Hotspur | | 1:1 (0:1) |
| Preston |
Football League Cup 1993/94, Second round |
| 22.09.1993 | | Burnley | – | Tottenham Hotspur | | 0:0 |
| Burnley |
Football League Cup 1991/92, Semifinals |
| 09.02.1992 | | Nottingham Forest | – | Tottenham Hotspur | | 1:1 (0:1) |
| Nottingham |
Football League Cup 1990/91, Fifth Round |
| 16.01.1991 | | Chelsea | – | Tottenham Hotspur | | 0:0 |
| London |
Football League Cup 1989/90, Fifth Round |
| 17.01.1990 | | Nottingham Forest | – | Tottenham Hotspur | | 2:2 |
| Nottingham |
Football League Cup 1989/90, Fourth Round |
| 22.11.1989 | | Tranmere Rovers | – | Tottenham Hotspur | | 2:2 |
| Birkenhead |
Football League Cup 1988/89, Third round |
| 01.11.1988 | | Tottenham Hotspur | – | Blackburn Rovers | | 0:0 |
| London |
Football League Cup 1988/89, Second round |
| 27.09.1988 | | Notts County | – | Tottenham Hotspur | | 1:1 |
| Nottingham |
Football League Cup 1986/87, Fifth Round |
| 27.01.1987 | | West Ham United | – | Tottenham Hotspur | | 1:1 |
| London |
Football League Cup 1985/86, Fourth Round |
| 26.11.1985 | | Portsmouth | – | Tottenham Hotspur | | 0:0 * |
| Portsmouth |
Football League Cup 1985/86, Fourth Round |
| 19.11.1985 | | Tottenham Hotspur | – | Portsmouth | | 0:0 |
| London |
Football League Cup 1984/85, Fourth Round |
| 21.11.1984 | | Sunderland | – | Tottenham Hotspur | | 0:0 |
| Sunderland |
Football League Cup 1982/83, Second round |
| 06.10.1982 | | Tottenham Hotspur | – | Brighton & Hove Albion | | 1:1 |
| London |
Football League Cup 1981/82, Semifinals |
| 03.02.1982 | | West Bromwich Albion | – | Tottenham Hotspur | | 0:0 |
| West Bromwich |
Football League Cup 1980/81, Third round |
| 24.09.1980 | | Tottenham Hotspur | – | Crystal Palace | | 0:0 |
| London |
Football League Cup 1978/79, Second round |
| 29.08.1978 |  | Swansea City | – | Tottenham Hotspur | | 2:2 |
| |
Football League Cup 1975/76, Fourth Round |
| 12.11.1975 | | Tottenham Hotspur | – | West Ham United | | 0:0 |
| London |
Football League Cup 1972/73, Semifinals |
| 30.12.1973 | | Tottenham Hotspur | – | Wolverhampton Wanderers | | 2:2 aet |
| London |
Football League Cup 1972/73, Fifth Round |
| 04.12.1972 | | Liverpool | – | Tottenham Hotspur | | 1:1 |
| Liverpool |
Football League Cup 1972/73, Third round |
| 11.10.1972 | | Tottenham Hotspur | – | Middlesbrough | | 0:0 aet * |
| London |
Football League Cup 1972/73, Third round |
| 03.10.1972 | | Middlesbrough | – | Tottenham Hotspur | | 1:1 |
| Middlesbrough |
Football League Cup 1971/72, Semifinals |
| 05.01.1972 | | Tottenham Hotspur | – | Chelsea | | 2:2 |
| London |
Football League Cup 1971/72, Fourth Round |
| 27.10.1971 | | Tottenham Hotspur | – | Preston North End | | 1:1 |
| London |
Football League Cup 1970/71, Semifinals |
| 16.12.1970 | | Bristol City | – | Tottenham Hotspur | | 1:1 |
| |
Football League Cup 1968/69, Semifinals |
| 04.12.1968 | | Tottenham Hotspur | – | Arsenal | | 1:1 |
| London |
