Football League Cup 2023/24, First Round |
 | 08.08.2023 |  | Barnsley | – | Tranmere Rovers | | 2:2 (1:1),
pen. 6:7 |
| Barnsley |
Football League Cup 2021/22, First Round |
| 10.08.2021 | | Bolton Wanderers | – | Barnsley | | 0:0,
pen. 5:4 |
| Bolton |
Football League Cup 2015/16, First Round |
| 11.08.2015 | | Scunthorpe United | – | Barnsley | | 1:1 aet
(0:0, 1:1),
pen. 6:7 |
| Scunthorpe |
Football League Cup 2013/14, First Round |
| 06.08.2013 | | Barnsley | – | Scunthorpe United | | 0:0 aet,
pen. 5:4 |
| Barnsley |
Football League Cup 2006/07, First Round |
| 22.08.2006 | | Blackpool | – | Barnsley | | 2:2 aet
(0:0, 1:1),
pen. 2:4 |
| Blackpool |
Football League Cup 2005/06, First Round |
| 23.08.2005 | | Preston North End | – | Barnsley | | 2:2 aet
(0:0, 1:1),
pen. 4:5 |
| Preston |
Football League Cup 1999/00, Second round |
| 21.09.1999 | | Stockport County | – | Barnsley | | 3:3 aet
(2:0, 2:2) |
| Stockport |
Football League Cup 1999/00, Second round |
| 14.09.1999 | | Barnsley | – | Stockport County | | 1:1 (1:1) |
| Barnsley |
Football League Cup 1999/00, First Round |
| 24.08.1999 | | Barnsley | – | Lincoln City | | 2:2 (0:1) |
| Barnsley |
Football League Cup 1998/99, Second round |
| 23.09.1998 | | Reading | – | Barnsley | | 1:1 (0:0) |
| Reading |
Football League Cup 1996/97, Second round |
| 17.09.1996 | | Barnsley | – | Gillingham | | 1:1 (0:0) |
| Barnsley |
Football League Cup 1994/95, First Round |
| 23.08.1994 | | Barnsley | – | Darlington | | 0:0 aet |
| Barnsley |
Football League Cup 1994/95, First Round |
| 17.08.1994 | | Darlington | – | Barnsley | | 2:2 (0:2) |
| Darlington |
Football League Cup 1993/94, Second round |
| 21.09.1993 | | Barnsley | – | Peterborough United | | 1:1 (0:0) |
| Barnsley |
Football League Cup 1992/93, First Round |
| 25.08.1992 | | Barnsley | – | Grimsby Town | | 1:1 aet,
pen. 3:5 |
| Barnsley |
Football League Cup 1992/93, First Round |
| 19.08.1992 | | Grimsby Town | – | Barnsley | | 1:1 (1:1) |
| Cleethorpes |
Football League Cup 1989/90, Second round |
| 03.10.1989 | | Blackpool | – | Barnsley | | 1:1 aet,
pen. 5:4 |
| Blackpool |
Football League Cup 1989/90, Second round |
| 19.09.1989 | | Barnsley | – | Blackpool | | 1:1 |
| Barnsley |
Football League Cup 1987/88, Second round |
| 22.09.1987 | | Barnsley | – | West Ham United | | 0:0 |
| Barnsley |
Football League Cup 1985/86, Second round |
| 08.10.1985 | | Barnsley | – | Newcastle United | | 1:1 |
| |
Football League Cup 1985/86, Second round |
| 25.09.1985 | | Newcastle United | – | Barnsley | | 0:0 |
| |
Football League Cup 1984/85, Second round |
| 09.10.1984 | | Barnsley | – | Grimsby Town | | 1:1 |
| |
Football League Cup 1981/82, Fifth Round |
| 12.01.1982 | | Liverpool | – | Barnsley | | 0:0 |
| Liverpool |
Football League Cup 1980/81, Second round |
| 26.08.1980 | | Mansfield Town | – | Barnsley | | 0:0 |
| |
Football League Cup 1978/79, First Round |
| 16.08.1978 | | Chesterfield | – | Barnsley | | 0:0 |
| |
Football League Cup 1976/77, First Round |
| 17.08.1976 | | Barnsley | – | York City | | 0:0 |
| |
Football League Cup 1976/77, First Round |
| 14.08.1976 | | York City | – | Barnsley | | 0:0 |
| |
Football League Cup 1975/76, First Round |
| 27.08.1975 | | Barnsley | – | Huddersfield Town | | 1:1 |
| |
Football League Cup 1973/74, First Round |
| 28.08.1973 | | Halifax Town | – | Barnsley | | 1:1 |
| |
Football League Cup 1972/73, First Round |
| 16.08.1972 | | Barnsley | – | Grimsby Town | | 0:0 |
| |
Football League Cup 1971/72, First Round |
| 18.08.1971 | | Barnsley | – | Hartlepool | | 0:0 |
| |
Football League Cup 1968/69, Second round |
| 03.09.1968 | | Barnsley | – | Millwall | | 1:1 |
| |
Football League Cup 1965/66, First Round |
| 01.09.1965 | | Doncaster Rovers | – | Barnsley | | 2:2 |
| |
Football League Cup 1963/64, First Round |
| 04.09.1963 | | Darlington | – | Barnsley | | 2:2 |
| |
Football League Cup 1962/63, First Round |
| 06.09.1962 | | Hartlepools United | – | Barnsley | | 1:1 |
| |
