Since 1966, Tottenham have entered the Football League Cup after choosing not to take part in the competition for the first few years after it was inaugurated in 1961. The club didn’t participate in the 1967-1968 season.
Here is the club’s record in the competition. Goal times given where known.
| Season 1966-1967 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 14.09.1966 | West Ham United | A | 3 | 0-1 | – | Hurst 7 | 34.000 |
| . | . | . | . | . | . | . | . |
| Season 1968-1969 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 04.09.1968 | Aston Villa | A | R2 | 4-1 | Chivers 41, Chivers 53, Chivers 57, Cliff Jones 76 | L. Martin 54 | 24,775 |
| 25.09.1968 | Exeter City | H | R3 | 6-3 | Greaves 19, Venables 32, Greaves 44, Pearce 63, Pearce 71, Greaves 89 | Mitten 15, Banks 30, Banks 80 | 25,798 |
| 16.10.1968 | Peterborough United | H | R4 | 1-0 | Greaves 52 | – | 28,378 |
| 30.10.1968 | Southampton | H | R5 | 1-0 | Collins 85 | – | 35,198 |
| 20.11.1968 | Arsenal | A | SF 1L | 0-1 | – | Radford 89 | 55,237 |
| 04.12.1968 | Arsenal | H | SF 2L | 1-1 | Greaves 67 | Radford 87 | 55,923 |
| . | . | . | . | . | . | . | . |
| Season 1969-1970 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 03.09.1969 | Wolverhampton Wanderers | A | R2 | 0-1 | – | McCalliog 8 | 34,017 |
| . | . | . | . | . | . | . | . |
| Season 1970-1971 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 09.09.1970 | Swansea City | H | 3 | 3-0 | Perryman, Peters 22, Morgan 30 | – | 15,848 |
| 07.10.1970 | Sheffield United | H | 3 | 2-1 | Pearce 42, Chivers 70 | Hemsley 45 | 23,559 |
| 28.10.1970 | West Bromwich Albion | H | 4 | 5-0 | Gilzean 44, Peters 69, Peters 76, Gilzean 78, Peters 89 | – | 32,598 |
| 18.11.1970 | Coventry City | H | 5 | 4-1 | Chivers 25, Chivers 62, Chivers 84, Gilzean 87 | O’Rourke 65 | 31,670 |
| 16.12.1970 | Bristol City | A | SF 1L | 1-1 | Gilzean 72 | Skirton 56 | 30,000 |
| 23.12.1970 | Bristol City | H | SF 2L | 2-0 (aet) | Chivers 98, Pearce 110 | – | 29,982 |
| 27.02.1971 | Aston Villa | Wembley | F | 2-0 | Chivers 78, Chivers 82 | – | 100,000 |
| . | . | . | . | . | . | . | . |
| Season 1971-1972 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 08.09.1971 | West Bromwich Albion | A | R2 | 1-0 | Pearce 78 | – | 26,203 |
| 06.10.1971 | Torquay United | A | R3 | 4-1 | Peters (p) 24, Chivers 34, Chivers 50, Pearce 81, | Stuckey 22 | 20,100 |
| 27.10.1971 | Preston North End | H | R4 | 1-1 | Chivers 40 | Lyall 84 | 30,338 |
| 08.11.1971 | Preston North End | A | R4r | 2-1 (aet) | Chivers 84, Perryman 112 | Spark 87 | 27,239 |
| 17.11.1971 | Blackpool | H | R5 | 2-0 | Peters 14, Chivers 69 | – | 30,039 |
| 22.12.1971 | Chelsea | A | SF 1L | 2-3 | Naylor 50, Chivers 52 | Osgood 38, Garland 75, Hollins (p) 86 | 43,330 |
| 05.01.1972 | Chelsea | H | SF 2L | 2-2 | Chivers 44, Peters (p) 81 | Garland 75, Hudson 89 | 52,755 |
| . | . | . | . | . | . | . | . |
| Season 1972-1973 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 06.09.1972 | Huddersfield Town | H | R2 | 2-1 | Chivers 45, Gilzean 65 | Pugh 82 | 21,422 |
| 03.10.1972 | Middlesbrough | A | R3 | 1-1 | Pearce 6 | Hickton 39 | 23,822 |
| 11.10.1972 | Middlesbrough | H | R3r | 0-0 (aet) | – | – | 19,256 |
| 30.10.1972 | Middlesbrough | H | R3r2 | 2-1 (aet) | Peters 32, Gilzean 117 | Hickton 8 | 19,287 |
| 01.11.1972 | Millwall | H | R4 | 2-0 | Peters 10, Perryman 14 | – | 28,904 |
| 04.12.1972 | Liverpool | A | R5 | 1-1 | Peters 54 | Hughes 78 | 48,677 |
| 06.12.1972 | Liverpool | H | R5r | 3-1 | Chivers 6, Pratt 12, Chivers 25 | Callaghan 85 | 35,565 |
| 20.12.1972 | Wolverhampton Wanderers | A | SF 1L | 2-1 | Peters 3, Pratt 15 | Hibbitt (p) 45 | 28,357 |
| 30.12.1972 | Wolverhampton Wanderers | H | SF 2L | 2-2 (aet) | Peters 71, Chivers 113 | Naylor o.g. 40, Richards 88 | 41,653 |
| 03.03.1973 | Norwich City | Wembley | F | 1-0 | Coates 72 | – | 100,000 |
| . | . | . | . | . | . | . | . |
| Season 1973-1974 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 08.10.1973 | QPR | A | R2 | 0-1 | – | England o.g. 32 | 23,353 |
| . | . | . | . | . | . | . | . |
| Season 1974-1975 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 11.09.1974 | Middlesbrough | A | R2 | 0-4 | – | Smith 36, Mills 42, Hickton (p) 57, Armstrong 72 | 15,216 |
| . | . | . | . | . | . | . | . |
| Season 1975-1976 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 09.09.1975 | Watford | A | R2 | 1-0 | Chris Jones 60 | – | 14,997 |
| 08.10.1975 | Crewe Alexandra | A | R3 | 2-0 | Pratt 20, Conn 32 | – | 10,561 |
| 12.11.1975 | West Ham United | H | R4 | 0-0 | – | – | 49,125 |
| 24.11.1975 | West Ham United | A | R4r | 2-0 (aet) | Duncan 101, W. Young 109 | – | 38,443 |
| 03.12.1975 | Doncaster Rovers | H | R5 | 7-2 | Duncan 15, Pratt 16, Duncan 32, Chivers 66, Chappell o.g. 52, Chivers, Duncan | Murray 9, Kitchen 51 | 25,702 |
| 14.01.1976 | Newcastle United | H | SF 1L | 1-0 | Pratt 31 | – | 40,215 |
| 21.01.1976 | Newcastle United | A | SF 2L | 1-3 | McAllister 71 | Gowling 3, McNulty 46, Keeley 66 | 49,657 |
| . | . | . | . | . | . | . | . |
| Season 1976-1977 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 31.08.1976 | Middlesbrough | A | R2 | 2-1 | Moores 23, Neighbour 48 | McAndrew 44 | 19,042 |
| 22.09.1976 | Wrexham | H | R3 | 2-3 | Hoddle 55, Moores 63 | Thomas 37, Thomas 42, Ashcroft 50 | 19,156 |
| . | . | . | . | . | . | . | . |
| Season 1977-1978 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 31.08.1977 | Wimbledon | H | R2 | 4-0 | Duncan 24, Duncan 32, Duncan 80, Osgood (p) 81 | – | 22,807 |
| 26.10.1977 | Coventry City | H | R3 | 2-3 | Pratt 39, G. Armstrong 89 | Graydon, Hutchison, Powell | 35,099 |
| . | . | . | . | . | . | . | . |
| Season 1978-1979 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 29.08.1978 | Swansea City | A | R2 | 2-2 | Hoddle (p) 43, G. Armstrong 65 | R. James 6, J. Charles 38 | 24,333 |
| 06.09.1978 | Swansea City | H | R2r | 1-3 | Villa 65 | Toshack 18, J. Charles 37, Curtis 71 | 33,672 |
| . | . | . | . | . | . | . | . |
| Season 1979-1980 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 29.08.1979 | Manchester United | H | R2 1L | 2-1 | Pratt 10, Hoddle 37 | Thomas 56 | 29,163 |
| 06.09.1979 | Manchester United | A | R2 2L | 1-3 | G. Armstrong 50 | Thomas 28, Coppell 52, Miller 58 | 48,292 |
| . | . | . | . | . | . | . | . |
| Season 1980-1981 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 27.08.1980 | Orient | A | R2 1L | 1-0 | Lacy 37 | – | 20,087 |
| 03.09.1980 | Orient | H | R2 2L | 3-1 | Archibald 13, Archibald 60, Crooks 90 | Jennings 48 | 25,443 |
| 24.09.1980 | Crystal Palace | H | R3 | 0-0 | – | – | 29,654 |
| 30.09.1980 | Crystal Palace | A | R3r | 3-1 (aet) | Hoddle 57, Crooks 108, Villa 115 | C. Allen (p) 49 | 26.409 |
| 04.11.1980 | Arsenal | H | R4 | 1-0 | Ardiles 26 | – | 42,521 |
| 02.12.1980 | West Ham United | A | R5 | 0-1 | – | Cross 81 | 36,235 |
| . | . | . | . | . | . | . | . |
| Season 1981-1982 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 07.10.1981 | Manchester United | H | R2 1L | 1-0 | Archibald 65 | – | 39,333 |
| 28.10.1981 | Manchester United | A | R2 2L | 1-0 | Hazard 7 | – | 55,890 |
| 11.11.1981 | Wrexham | H | R3 | 2-0 | Hoddle 21, Hughton 86 | – | 24,084 |
| 02.12.1981 | Fulham | H | R4 | 1-0 | Hazard 41 | – | 30,214 |
| 18.01.1982 | Nottingham Forest | H | R5 | 1-0 | Ardiles 59 | – | 31,192 |
| 03.02.1982 | West Bromwich Albion | A | SF 1L | 0-0 | – | – | 32,100 |
| 10.02.1982 | West Bromwich Albion | H | SF 2L | 1-0 | Hazard 55 | – | 47,421 |
| 13.03.1982 | Liverpool | Wembley | F | 1-3 (aet) | Archibald 11 | Whelan 87, Whelan 111, Rush 119 | 100,000 |
| . | . | . | . | . | . | . | . |
| Season 1982-1983 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 06.10.1982 | Brighton & Hove Albion | H | R2 1L | 1-1 | Brooke (p) 89 | Clemence o.g. 40 | 20,416 |
| 26.10.1982 | Brighton & Hove Albion | A | R2 2L | 1-0 | Crooks 70 | – | 20,763 |
| 09.11.1982 | Gillingham | A | R3 | 4-2 | Crooks 15, Archibald 43, Archibald 48, Crooks 90 | Johnson 26, Price 68 | 14,446 |
| 01.12.1982 | Luton Town | H | R4 | 1-0 | Villa 64 | – | 27,461 |
| 19.01.1983 | Burnley | H | R5 | 1-4 | Gibson 46 | Roberts o.g. 65, Hamilton 75, Roberts o.g. 86, Hamilton 89 | 30,771 |
| . | . | . | . | . | . | . | . |
| Season 1983-1984 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 05.10.1983 | Lincoln City | H | R2 1L | 3-1 | Archibald 16, Houghton o.g. 33, Galvin 87 | Shipley 53 | 20,241 |
| 26.10.1983 | Lincoln City | A | R2 2L | 1-2 | Falco 76 | J. Thomas 43, Jack (p) 80 | 12,088 |
| 09.11.1983 | Arsenal | H | R3 | 1-2 | Hoddle (p) 51 | Nicholas 34, Woodcock 41 | 48,200 |
| . | . | . | . | . | . | . | . |
| Season 1984-1985 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 26.09.1984 | Halifax Town | A | R2 1L | 5-1 | Falco 27, Falco 56, Crooks 69, Crooks 77, Crooks 83 | Gallagher 78 | 7,027 |
| 09.10.1984 | Halifax Town | H | R2 2L | 4-0 | Hazard 8, Hughton 36, Crooks 66, Hazard 76 | – | 14,802 |
| 31.10.1984 | Liverpool | H | R3 | 1-0 | C. Allen 6 | – | 38,690 |
| 21.11.1984 | Sunderland | A | R4 | 0-0 | – | – | 27,421 |
| 05.12.1984 | Sunderland | H | R4r | 1-2 | Roberts (p) 5 | Miller o.g. 23, Chisholm 47 | 25,835 |
| . | . | . | . | . | . | . | . |
| Season 1985-1986 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 23.09.1985 | Orient | A | R2 1L | 0-2 | – | Godfrey 62, Godfrey 77 | 13,828 |
| 30.10.1985 | Orient | H | R2 2L | 4-0 | Roberts 44, Roberts 57, Galvin 66, Waddle 72 | – | 21,046 |
| 06.11.1985 | Wimbledon | H | R3 | 2-0 | Mabbutt 56, Leworthy 75 | – | 16,919 |
| 20.11.1985 | Portsmouth | H | R4 | 0-0 | – | – | 28,619 |
| 27.11.1985 | Portsmouth | A | R4r | 0-0 | – | – | 28,100 |
| 10.12.1985 | Portsmouth | A | R4r2 | 0-1 | – | Blake 44 | 26,306 |
| . | . | . | . | . | . | . | . |
| Season 1986-1987 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 23.09.1986 | Barnsley | A | R2 1L | 3-2 | Waddle 4, Roberts, C. Allen | Gray 25, Gray (p) 75 | 9,979 |
| 08.10.1986 | Barnsley | H | R2 2L | 5-3 | Close 14, Hoddle 31, Hoddle 43, Galvin 60, C. Allen 84 | Beresford 32, May 68, Chandler 86 | 12,299 |
| 29.10.1986 | Birmingham City | H | R3 | 5-0 | Waddle 24, C. Allen 45, C. Allen 48, Roberts 63, Hoddle 85 | – | 15,542 |
| 26.11.1986 | Cambridge United | A | R4 | 3-1 | C. Allen, Close, Waddle | Cooper | 10,033 |
| 27.01.1987 | West Ham United | A | R5 | 1-1 | C. Allen 38 | Cottee 49 | 28,648 |
| 02.02.1987 | West Ham United | H | R5r | 5-0 | Claesen 6, Hoddle 71, C. Allen 80, C. Allen (p) 85, C. Allen 88 | – | 41,995 |
| 08.02.1987 | Arsenal | A | SF 1L | 1-0 | C. Allen 39 | – | 41,306 |
| 01.03.1987 | Arsenal | H | SF 2L | 1-2 (aet) | C. Allen 11 | Anderson 50, Quinn 64 | 37,099 |
| 04.03.1987 | Arsenal | H | SFr | 1-2 | C. Allen 62 | Allinson 83, Rocastle 90 | 41,005 |
| . | . | . | . | . | . | . | . |
| Season 1987-1988 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 23.09.1987 | Torquay United | A | R2 1L | 0-1 | – | Dawson 86 | 5,000 |
| 07.10.1987 | Torquay United | H | R2 2L | 3-1 | Claesen 4, Cole o.g. 36, Claesen 80 | . | 20,970 |
| 28.10.1987 | Aston Villa | A | R3 | 1-2 | Ardiles 64 | McInally 8, Aspinall 78 | 29,114 |
| . | . | . | . | . | . | . | . |
| Season 1988-1989 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 27.09.1988 | Notts County | A | R2 1L | 1-1 | Samways 75 | Birtles 46 | 9,279 |
| 11.10.1988 | Notts County | H | R2 2L | 2-1 | Fenwick (p) 61, Gascoigne 80 | . | 14,953 |
| 01.11.1988 | Blackburn Rovers | H | R3 | 0-0 | – | . | 18,814 |
| 09.11.1988 | Blackburn Rovers | A | R3r | 2-1 (aet) | M. Thomas 106, Stewart 112 | Dawson 109 | 12,965 |
| 29.11.1988 | Southampton | A | R4 | 1-2 | Osman o.g. 62 | Cockerill 49, Moore 55 | 17,375 |
| . | . | . | . | . | . | . | . |
| Season 1989-1990 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 20.09.1989 | Southend United | H | R2 1L | 1-0 | Fenwick 74 | – | 15,734 |
| 04.10.1989 | Southend United | A | R2 2L | 2-3 (aet) | P. Allen 42, Nayim 55 | Martin 4, Bennett 40, Bennett 87 | 10,400 |
| 25.10.1989 | Manchester United | A | R3 | 3-0 | Lineker 25, Samways 47, Nayim 88 | – | 45,759 |
| 22.11.1989 | Tranmere Rovers | A | R4 | 2-2 | Gascoigne 31, Higgins o.g. 68 | Vickers 50, Steel 62 | 13,789 |
| 29.11.1989 | Tranmere Rovers | H | R4r | 4-0 | Howells 29, Stewart 75, Mabbutt 80, P. Allen 84 | – | 23,724 |
| 17.01.1990 | Nottingham Forest | A | R5 | 2-2 | Lineker 60, Sedgley 80 | Crosby 36, Parker 56 | 30,044 |
| 24.01.1990 | Nottingham Forest | H | R5r | 2-3 | Lineker 12, Lineker 80 | Clough 27, Crosby 29, Parker 70 | 32,357 |
| . | . | . | . | . | . | . | . |
| Season 1990-1991 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 26.09.1990 | Hartlepool United | H | R2 1L | 5-0 | Lineker 2, Gascoigne 26, Gascoigne 75, Gascoigne 81 (p), Gascoigne 86 | – | 19,760 |
| 09.10.1990 | Hartlepool United | A | R2 2L | 2-1 | Stewart 10, Stewart 47 | Dalton 60 | 9,700 |
| 30.10.1990 | Bradford City | H | R3 | 2-1 | Gascoigne, Stewart | Oliver 14 | 25,451 |
| 27.11.1990 | Sheffield United | A | R4 | 2-0 | Gascoigne 25, Stewart 27 | – | 25,824 |
| 16.01.1991 | Chelsea | A | R5 | 0-0 | – | – | 30,178 |
| 23.01.1991 | Chelsea | H | R5r | 0-3 | – | Townsend 16, Dixon 70, Wise (p) 83 | 33,861 |
| . | . | . | . | . | . | . | . |
| Season 1991-1992 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 25.09.1991 | Swansea City | A | R2 1L | 0-1 | – | Gilligan 88 | 11,416 |
| 09.10.1991 | Swansea City | H | R2 2L | 5-1 | P. Allen 18, Lineker (p) 54, Brazil o.g. 60, Stewart 65, Samways 79 | Chapple 81 | 20,198 |
| 29.10.1991 | Grimsby Town | A | R3 | 3-0 | Howells 32, Lineker 79, Durie 83 | – | 17,017 |
| 04.12.1991 | Coventry City | A | R4 | 2-1 | P. Allen 44, Durie 62 | Furlong 67 | 20,095 |
| 08.01.1992 | Norwich City | H | R5 | 2-1 | Walsh 77, Lineker 85 | Fleck 31 | 29,471 |
| 09.02.1992 | Nottingham Forest | A | SF 1L | 1-1 | Lineker (p) 24 | Sheringham 62 | 21,402 |
| 01.03.1992 | Nottingham Forest | H | SF 2L | 1-2 (aet) | Lineker 16 | Glover 11, Keane 101 | 28,216 |
| . | . | . | . | . | . | . | . |
| Season 1992-1993 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 22.09.1992 | Brentford | A | R2 1L | 3-1 | Sheringham 41, Watson 61, Durie 73 | Blissett 56 | 19,365 |
| 07.10.1992 | Brentford | H | R2 2L | 4-2 | Anderton 3, Sheringham 8, Turner 51, Sheringham (p) 81 | Blissett 21, Millen 85 | 11,445 |
| 28.10.1992 | Manchester City | A | R3 | 1-0 | Samways 14 | – | 18,399 |
| 02.12.1992 | Nottingham Forest | H | R4 | 0-2 | – | . | 22,312 |
| . | . | . | . | . | . | . | . |
| Season 1993-1994 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 22.09.1993 | Burnley | A | R2 1L | 0-0 | – | – | 16,844 |
| 06.10.1993 | Burnley | H | R2 2L | 3-1 | Sheringham 2, Howells | . | 20,614 |
| 27.10.1993 | Derby County | A | R3 | 1-0 | Barmby 71 | – | 19,885 |
| 01.12.1993 | Blackburn Rovers | H | R4 | 1-0 | S. Campbell 84 | – | 22,295 |
| 12.01.1994 | Aston Villa | H | R5 | 1-2 | Caskey 63 | Houghton 56, Barrett 68 | 31,408 |
| . | . | . | . | . | . | . | . |
| Season 1994-1995 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 21.09.1994 | Watford | A | R2 1L | 6-3 | Anderton 4, Klinsmann 17, Klinsmann 34, Klinsmann 45, Sheringham 75, Dumitrescu 88 | Ramage 1, Mooney 66, Mabbutt o.g. 89 | 13,695 |
| 04.10.1994 | Watford | H | R2 2L | 2-3 | Barmby 30, Klinsmann 63 | Foster 14, Nogan 47, Nogan 74 | 17,798 |
| 26.10.1994 | Notts County | A | R3 | 0-3 | – | Agana 17, McSwegan 20, McSwegan 72 | 16,952 |
| . | . | . | . | . | . | . | . |
| Season 1995-1996 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 20.09.1995 | Chester City | H | R2 1L | 4-0 | C. Armstrong 20, C. Armstrong 30, Sheringham 43, Rosenthal 90 | – | 17,645 |
| 04.10.1995 | Chester City | A | R2 2L | 3-1 | Sheringham 35, Howells 45, Sheringham 68 | Bishop 21 | 5,372 |
| 25.10.1995 | Coventry City | A | R3 | 2-3 | C. Armstrong 2, Busst o.g. 20 | Ndlovu (p) 55, Busst 61, Salako 76 | 18,227 |
| . | . | . | . | . | . | . | . |
| Season 1996-1997 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 17.09.1996 | Preston North End | A | R2 1L | 1-1 | Anderton 2 | Holt 90 | 16,258 |
| 25.09.1996 | Preston North End | H | R2 2L | 3-0 | Anderton 31, P. Allen 62, P. Allen 76 | – | 10,080 |
| 24.10.1996 | Sunderland | H | R3 | 2-1 | C. Armstrong 71, S. Campbell 90 | Ball 31 | 24,867 |
| 27.11.1996 | Bolton Wanderers | A | R4 | 1-6 | Sheringham 19 | McGinlay 6, McGinlay 37, Taggart 60, McGinlay (p) 74, Blake 79, S. Taylor 86 | 18,621 |
| . | . | . | . | . | . | . | . |
| Season 1997-1998 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 17.09.1997 | Carlisle United | H | R2 1L | 3-2 | Fenn 1, Fox 72, Mahorn 77 | . | 19,255 |
| 30.09.1997 | Carlisle United | A | R2 2L | 2-0 | Ginola (p) 43, C. Armstrong 50 | – | 13,571 |
| 15.10.1997 | Derby County | H | R3 | 1-2 | Ginola 22 | Wanchope 27, Wanchope 71 | 20,390 |
| . | . | . | . | . | . | . | . |
| Season 1998-1999 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 15.09.1998 | Brentford | A | R2 1L | 3-2 | Carr 44, Dominguez 53, Vega | Scott 28, Freeman 66 | 11,831 |
| 23.09.1998 | Brentford | H | R2 2L | 3-2 | Nielsen 24, S. Campbell, C. Armstrong | Scott 1, Owusu 74 | 22,980 |
| 27.10.1998 | Northampton Town | A | R3 | 3-1 | C. Armstrong 39, Campbell 47, C. Armstrong 83 | Parrish 30 | 7,442 |
| 10.11.1998 | Liverpool | A | R4 | 3-1 | Iversen 2, Scales 20, Nielsen 63 | Owen 81 | 20,772 |
| 02.12.1998 | Manchester United | H | R5 | 3-1 | C. Armstrong 48, C. Armstrong 55, Ginola 86 | Sheringham 71 | 35,702 |
| 27.01.1999 | Wimbledon | H | SF 1L | 0-0 | . | – | 35,997 |
| 16.02.1999 | Wimbledon | A | SF 2L | 1-0 | Iversen 39 | – | 25,204 |
| 21.03.1999 | Leicester City | Wembley | F | 1-0 | Nielsen 90+2 | – | 77,892 |
| . | . | . | . | . | . | . | . |
| Season 1999-2000 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 13.10.1999 | Crewe Alexandra | H | R3 | 3-1 | Leonhardsen 55, Ginola 63, Sherwood 88 | S. Smith (p) 70 | 25,486 |
| 01.12.1999 | Fulham | A | R4 | 1-3 | Iversen 43 | Hayles 10, Collins 44, Horsfield 77 | 18,134 |
| . | . | . | . | . | . | . | . |
| Season 2000-2001 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 19.09.2000 | Brentford | A | R2 1L | 0-0 | – | – | 8,580 |
| 26.09.2000 | Brentford | H | R2 2L | 2-0 | Leonhardsen 53, Iversen 81 | – | 26,909 |
| 31.10.2000 | Birmingham City | H | R3 | 1-3 | Anderton (p) | Adebola 14, Adebola 36, Burchill 43 | 27,096 |
| . | . | . | . | . | . | . | . |
| Season 2001-2002 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 13.09.2000 | Torquay United | H | R2 | 2-0 | King 61, Ferdinand 69 | . | 20,347 |
| 09.10.2000 | Tranmere Rovers | A | R3 | 4-0 | Sheringham (p) 21, Anderton 39, Poyet 49, Rebrov 81 | – | 12,386 |
| 29.11.2000 | Fulham | A | R4 | 2-1 | Rebrov 15, S. Davies 86 | Hayles 45 | 17,006 |
| 11.12.2000 | Bolton Wanderers | H | R5 | 6-0 | S. Davies 21, Ferdinand 29, Ferdinand 30, Ferdinand 38, Barness o.g. 79, Iversen 84 | – | 28,430 |
| 09.01.2001 | Chelsea | A | SF 1L | 1-2 | Ferdinand 65 | Hasslebaink 10, Hasslebaink 77 | 37,264 |
| 23.01.2001 | Chelsea | H | SF 2L | 5-1 | Iversen 1m 45s, Sherwood 33, Sheringham 50, S. Davies 76, Rebrov 87 | Forsell 90 | 34,799 |
| 24.02.2001 | Blackburn Rovers | Cardiff | F | 1-2 | Ziege 89 | Jansen 25, Cole 69 | 72,500 |
| . | . | . | . | . | . | . | . |
| Season 2002-2003 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 01.10.2002 | Cardiff City | H | R2 | 1-0 | Sheringham 29 | – | 23,732 |
| 06.11.2002 | Burnley | A | R3 | 1-2 | Poyet 17 | Blake 57, Davis 61 | 13,512 |
| . | . | . | . | . | . | . | . |
| Season 2003-2004 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 24.09.2003 | Coventry City | A | R2 | 3-0 | Kanoute 13, Keane 23, Ricketts 85 | – | 15,474 |
| 29.10.2003 | West Ham United | H | R3 | 1-0 (aet) | Zamora 91 | – | 36,053 |
| 03.12.2003 | Manchester City | H | R4 | 3-1 | Anderton 8, Postiga 31, Kanoute 90 | . | 31,727 |
| 17.12.2003 | Middlesbrough | H | R5 | 1-1 (aet) (lost 4-5 pens) |
Anderton 2 | Ricketts 86 | 25,307 |
| . | . | . | . | . | . | . | . |
| Season 2004-2005 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 22.09.2004 | Oldham | A | R2 | 6-0 | Kanoute 37, Keane 64, Defoe 71, Bunjevcevic 87, Gardner 90, Kanoute 90 | – | 8,548 |
| 27.10.2004 | Bolton Wanderers | A | R3 | 4-3 (aet) | Defoe 44, Bunjevcevic 84, Brown 94, Defoe 103 | King o.g. 27, Okocha (p) 75, Ferdinand 105 | 18,037 |
| 09.11.2004 | Burnley | A | R4 | 3-0 | Keane 31, Keane 52, Defoe 58 | – | 10,639 |
| 01.12.2004 | Liverpool | H | R5 | 1-1 (aet) (lost 3-4 pens) |
Defoe 108 | Sinama-Pongolle (p) 117 | 36,100 |
| . | . | . | . | . | . | . | . |
| Season 2005-2006 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 20.09.2005 | Grimsby Town | A | R2 | 0-1 | – | Kalala 89 | 8,206 |
| . | . | . | . | . | . | . | . |
| Season 2006-2007 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 23.10.2006 | Milton Keynes Dons | A | R3 | 5-0 | Mido 36, Defoe 44, Defoe 51, Mido 60, Keane 90+2 | – | 8,306 |
| 08.11.2006 | Port Vale | H | R4 | 3-1 (aet) | Huddlestone 80, Huddlestone 99, Defoe 107 | Constantine 84 | 34,560 |
| 20.12.2006 | Southend United | H | R5 | 1-0 (aet) | Defoe 115 | – | 35,811 |
| 24.01.2007 | Arsenal | H | SF 1L | 2-2 | Berbatov 14, Baptista o.g. 21 | Baptista 64, Baptista 77 | 35,485 |
| 31.01.2007 | Arsenal | A | SF 2L | 1-3 (aet) | Mido 85 | Adebayor 77, Aladiere 107, Chimbonda o.g. 113 | 59,872. |
| . | . | . | . | . | . | . | . |
| Season 2007-2008 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 26.09.2007 | Middlesbrough | H | R3 | 2-0 | Bale 72, Huddlestone 76 | – | 30,084 |
| 31.10.2007 | Blackpool | H | R4 | 2-0 | Keane 18, Chimbonda 58 | – | 32,196 |
| 18.12.2007 | Manchester City | A | R5 | 2-0 | Defoe 5, Malbranque 82 | – | 38,564 |
| 09.01.2008 | Arsenal | A | SF 1L | 1-1 | Jenas 37 | Walcott 79 | 53,163 |
| 22.02.2008 | Arsenal | H | SF 2L | 5-1 | Jenas 3, Bendtner o.g. 27, Keane 48, Lennon 60, Malbranque 90 | Adebayor 70 | 35,979 |
| 24.02.2008 | Chelsea | Wembley | F | 2-1 (aet) | Berbatov (p) 70, Woodgate 90+4 | Drogba 39 | 87,660 |
| . | . | . | . | . | . | . | . |
| Season 2008-2009 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 24.09.2008 | Newcastle United | A | R3 | 2-1 | Pavlyuchenko 62, O’Hara 66 | Owen 90 | 20,577 |
| 12.11.2008 | Liverpool | H | R4 | 4-2 | Pavlyuchenko 38, F. Campbell 42, F. Campbell 45, Pavlyuchenko 52 | Plessis 49, Hyypia 63 | 33,242 |
| 03.12.2008 | Watford | A | R5 | 2-1 | Pavlyuchenko (p) 45+2, Bent 76 | Priskin 13 | 16,501 |
| 06.01.2009 | Burnley | H | SF 1L | 4-1 | Dawson 47, O’Hara 52, Pavlyuchenko 65, Duff o.g. 68 | Paterson 15 | 31,377 |
| 21.01.2009 | Burnley | A | SF 2L | 2-3 (aet) | Pavlyuchenko 118, Defoe 120 | Blake 34, McCann 73, Rodriguez 88 | 19,533 |
| 01.03.2009 | Manchester United | Wembley | F | 0-0 (aet) (lost 1-4 pens) |
– | – | 88,217 |
| . | . | . | . | . | . | . | . |
| Season 2009-2010 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 26.08.2009 | Doncaster Rovers | A | R2 | 5-1 | Huddlestone 9, O’Hara 11, Crouch 37, Bentley 52, Pavlyuchenko 69 | Woods (p) 61 | 12,923 |
| 23.09.2009 | Preston North End | A | R3 | 5-1 | Crouch 14, Defoe 37, Crouch 77, Keane 87, Crouch 90+2 | – | 16,533 |
| 27.10.2009 | Everton | H | R4 | 2-0 | Huddlestone 32, Keane 57 | – | 35,843 |
| 01.12.2009 | Manchester United | A | R5 | 0-2 | – | Gibson 17, Gibson 38 | 57,212 |
| . | . | . | . | . | . | . | . |
| Season 2010-2011 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 21.09.2010 | Arsenal | H | R3 | 1-4 (aet) | Keane 49 | Lansbury 15, Nasri (p) 92, Nasri (p) 95, Arshavin 105 | 35,883 |
| . | . | . | . | . | . | . | . |
| Season 2011-2012 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 20.09.2011 | Stoke City | A | R3 | 0-0 (aet) (lost 6-7 pens) | – | – | 15,023 |
| . | . | . | . | . | . | . | . |
| Season 2012-2013 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 26.09.2012 | Carlisle United | A | R3 | 3-0 | Vertonghen 37, Townsend 53, Sigurdsson 89 | – | 12,625 |
| 31.10.2012 | Norwich City | A | R4 | 1-2 | Bale 66 | Vertonghen o.g. 84, Jackson 87 | 16,465 |
| . | . | . | . | . | . | . | . |
| Season 2013-2014 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 24.09.2013 | Aston Villa | A | R3 | 4-0 | Defoe 45+1, Paulinho 49, Chadli 86, Defoe 90 | – | 22,975 |
| 30.10.2013 | Hull City | H | R4 | 2-2 (aet) (won 8-7 pens) | Sigurdsson 16, Kane 108 | . | 35,617 |
| 18.12.2013 | West Ham United | H | R5 | 1-2 | Adebayor 67 | . | 34,080 |
| . | . | . | . | . | . | . | . |
| Season 2014-2015 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 24.09.2014 | Nottingham Forest | H | R3 | 3-1 | Mason 73, Soldado 84, Kane 90+2 |
Grant 61 | 31,912 |
| 29.10.2014 | Brighton & Hove Albion | H | R4 | 2-0 | Lamela 54m 11s, Kane 74m 08s | – | 33,357 |
| 17.12.2014 | Newcastle United | H | R5 | 4-0 | Bentaleb 19, Chadli 47, Kane 64, Soldado 71 | – | 24,677 |
| 21.01.2015 | Sheffield United | H | SF 1L | 1-0 | Townsend (p) 73m 19s | – | 35,323 |
| 28.01.2015 | Sheffield United | A | SF 2L | 2-2 | Eriksen 27m 21s, Eriksen 87m 14s | Adams 76m 29s, Adams 78m 49s | 30,236 |
| 01.03.2015 | Chelsea | Wembley | F | 0-2 | – | Terry 44m 07s, Walker o.g. 55m 49s | 89,297 |
| . | . | . | . | . | . | . | . |
| Season 2015-2016 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 23.09.2015 | Arsenal | H | R3 | 1-2 | Chambers o.g. 56m 30s | Flamini 26m 23s, Flamini 78m 21s | 35,687 |
| . | . | . | . | . | . | . | . |
| Season 2016-2017 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 21.09.2016 | Gillingham | H | R3 | 5-0 | Eriksen 31, Eriksen 48, Jansson (p) 51, Onomah 65, Lamela 68 | – | 26,244 |
| 25.10.2016 | Liverpool | A | R4 | 1-2 | Jansson (p) 75m 21s | Sturridge 08m 20s, Sturridge 63m 37s | 53,051 |
| . | . | . | . | . | . | . | . |
| Season 2017-2018 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 19.09.2017 | Barnsley | H | R3 | 1-0 | Alli 65 | – | 23,826 |
| 25.10.2017 | West Ham United | H | R4 | 2-3 | Sissoko 05m 13s, Alli 36m 22s | Ayew 54m 44s, Ayew 59m 57s, Ogbonna 69m 11s | 36,168 |
| . | . | . | . | . | . | . | . |
| Season 2018-2019 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 26.09.2018 | Watford | H ° | R3 | 2-2 (won 4-2 pens) |
Alli (p) 81, Lamela 85 | Success 45m 37s, Davies o.g. 88 | 23,650 |
| 31.10.2018 | West Ham United | A | R4 | 3-1 | Son 16, Son 54, Llorente 75 | Perez 71 | 50,270 |
| 19.12.2018 | Arsenal | A | R5 | 2-0 | Son 12m 48s, Alli 58m 48s | – | 59,016 |
| 09.01.2019 | Chelsea | H | SF 1L | 1-0 | Kane 26m 01s | – | 44,301 |
| 24.01.2019 | Chelsea | A | SF 2L | 1-2 (aet) (lost 2-4 pens) |
Llorente 49m 50s | Kante 26m 43s, Hazard 37m 47s. | 38,610 |
| . | . | . | . | . | . | . | . |
| ° | Played at Stadium MK | ||||||
| . | . | . | . | . | . | . | . |
| Season 2019-2020 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 24.09.2019 | Colchester United | A | 3 | 0-0 (aet) (lost 3-4 pens) |
– | – | 9.481 |
| . | . | . | . | . | . | . | . |
| Season 2020-2021 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 22.09.2020 | Leyton Orient | A | R3 | w/o ‡ | – | – | 0 |
| 29.09.2020 | Chelsea | H | R4 | 1-1 (aet) (won 5-4 pens) |
Lamela 82m 69s | Werner 18m 18s | 0 |
| 23.12.2020 | Stoke City | A | R5 | 3-1 | Bale 21m 34s, Davies 69m 58s, Kane 80m 44s | Thompson 53m 47s | 0 |
| 05.01.2021 | Brentford | H | SF | 2-0 | Sissoko 11m 52s, Son 69m 15s | – | 0 |
| 25.04.2021 | Manchester City | Wembley | F | 0-1 | – | Laporte 81m 26s | 7,773 |
| . | . | . | . | . | . | . | . |
| ‡ Leyton Orient unable to fulfil fixture because players suffering from Covid-19. | |||||||
| . | . | . | . | . | . | . | . |
| Season 2021-2022 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 22.09.2021 | Wolverhampton Wanderers | A | R3 | 2-2 (won 3-2 pens) |
Ndombele 14, Kane 23 | Dendoncker 38, Podence 58 | 28,798 |
| 29.09.2021 | Burnley | A | R4 | 1-0 | Moura 67m 09s | – | 14,637 |
| 23.11.2021 | West Ham United | H | R5 | 2-1 | Bergwijn 28m 09s, Moura 33m 50s | Bowen 31m 26s | 40,031 |
| 22.12.2021 | Chelsea | H | SF 1L | 0-2 | Havertz 5, Davies o.g. 34 | . | 37,868 |
| 25.04.2022 | Chelsea | A | SF 2L | 0-1 | Rudiger 18 | . | 45,603 |
| – | |||||||
| Season 2022-2023 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 09.11.2022 | Nottingham Forest | A | 3 | 0-2 | – | Lodi 49m 02s, Lingard 56m 31s | 28,384 |
| – | |||||||
| Season 2023-2024 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 29.08.2023 | Fulham | A | 2 | 1-1 (lost 3-5 pens) |
Richarlison 55m 22s | van de Ven o.g. 18m 42s | 21,043 |
| – | |||||||
| Season 2024-2025 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 18.09.2024 | Coventry City | A | 3 | 2-1 | Spence 87m 04s, Johnson 90+1m 33s | Asante 62m 41s | 24,606 |
| 30.10.2024 | Manchester City | H | 4 | 2-1 | Werner 04m 59s, Sarr 24m 52s | Nunes 45+3m 31s | 60,797 |
| 19.12.2025 | Manchester United | H | 5 | 4-3 | Solanke 14m 21s, Kulusevski 45m 47s, Solanke 53m 30s, Son 87m 19s | Zirkzee 52m 48s, Diallo 69m 46s, Evans 90+3m 48s | 57,409 |
| 08.01.2025 | Liverpool | H | SF 1L | 1-0 | Bergvall 85m 09s | – | 59,037 |
| 06.02.2025 | Liverpool | A | SF L2 | 0-4 | – | Gakpo 34, Salah (p) 51, Szoboszlai 75, van Dijk 80 | 60,395 |
| . | . | . | . | . | . | . | . |
| Season 2025-2026 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| 23.09.2025 | Doncaster Rovers | H | 3 | 3-0 | Palhinha 13m 23s, McGrath (o.g.) 16m 12s, Johnson 90+3m 55s | – | 42,473 |
| 29.10.2025 | Newcastle United | A | 4 | 0-2 | – | Schar 23m 30s, Woltemade 49m 08s | . |
| . | . | . | . | . | . | . | . |
| Season 2026-2027 | |||||||
| Date | Opponent | Venue | Round | Score | THFC scorers | Opposition scorers | Attendance |
| ..2026 | – | – | 3 | – | . | . | , |
Credit to the THFC Database for some of the scorers and goal times.