Football League Cup 2022/23, First Round |
 | 10.08.2022 |  | Middlesbrough | – | Barnsley | | 0:1 (0:0) |
| Middlesbrough |
Football League Cup 2020/21, Second round |
| 15.09.2020 | | Middlesbrough | – | Barnsley | | 0:2 (0:2) * |
| Middlesbrough |
Football League Cup 2020/21, First Round |
| 05.09.2020 | | Barnsley | – | Nottingham Forest | | 1:0 (0:0) * |
| Barnsley |
Football League Cup 2017/18, Second round |
| 12.09.2017 | | Barnsley | – | Derby County | | 3:2 (1:2) |
| Barnsley |
Football League Cup 2017/18, First Round |
| 08.08.2017 | | Barnsley | – | Morecambe | | 4:3 (2:1) |
| Barnsley |
Football League Cup 2012/13, First Round |
| 11.08.2012 | | Rochdale | – | Barnsley | | 3:4 aet
(1:1, 2:2) |
| Rochdale |
Football League Cup 2009/10, Third round |
| 22.09.2009 | | Barnsley | – | Burnley | | 3:2 (2:1) |
| Barnsley |
Football League Cup 2009/10, Second round |
| 25.08.2009 | | Reading | – | Barnsley | | 1:2 (0:0) |
| Reading |
Football League Cup 2009/10, First Round |
| 11.08.2009 | | Lincoln City | – | Barnsley | | 0:1 (0:0) |
| Lincoln |
Football League Cup 2007/08, First Round |
| 14.08.2007 | | Barnsley | – | Darlington | | 2:1 (0:0) |
| Barnsley |
Football League Cup 2004/05, First Round |
| 24.08.2004 | | Darlington | – | Barnsley | | 0:2 (0:1) |
| Darlington |
Football League Cup 2001/02, Second round |
| 11.09.2001 | | Colchester United | – | Barnsley | | 1:3 (0:1) |
| Colchester |
Football League Cup 2001/02, First Round |
| 21.08.2001 | | Barnsley | – | Halifax Town | | 2:0 (1:0) |
| Barnsley |
Football League Cup 2000/01, Second round |
| 26.09.2000 | | Crewe Alexandra | – | Barnsley | | 0:3 (0:1) |
| Crewe |
Football League Cup 2000/01, Second round |
| 19.09.2000 | | Barnsley | – | Crewe Alexandra | | 4:0 (1:0) |
| Barnsley |
Football League Cup 2000/01, First Round |
| 05.09.2000 | | Barnsley | – | Rotherham United | | 3:2 (0:1) |
| Barnsley |
Football League Cup 2000/01, First Round |
| 22.08.2000 | | Rotherham United | – | Barnsley | | 0:1 (0:1) |
| Rotherham |
Football League Cup 1999/00, Third round |
| 12.10.1999 | | Bradford City | – | Barnsley | | 2:3 (1:2) |
| Bradford |
Football League Cup 1999/00, First Round |
| 10.08.1999 | | Lincoln City | – | Barnsley | | 2:4 (1:3) |
| Lincoln |
Football League Cup 1998/99, Third round |
| 27.10.1998 | | Barnsley | – | AFC Bournemouth | | 2:1 (1:0) |
| Barnsley |
Football League Cup 1998/99, Second round |
| 15.09.1998 | | Barnsley | – | Reading | | 3:0 (1:0) |
| Barnsley |
Football League Cup 1998/99, First Round |
| 18.08.1998 | | Barnsley | – | Scarborough | | 3:0 (2:0) |
| Barnsley |
Football League Cup 1998/99, First Round |
| 12.08.1998 | | Scarborough | – | Barnsley | | 0:1 (0:1) |
| Scarborough |
Football League Cup 1997/98, Second round |
| 30.09.1997 | | Barnsley | – | Chesterfield | | 4:1 (2:0) |
| Barnsley |
Football League Cup 1997/98, Second round |
| 16.09.1997 | | Chesterfield | – | Barnsley | | 1:2 (0:0) |
| Chesterfield |
Football League Cup 1996/97, First Round |
| 03.09.1996 | | Barnsley | – | Rochdale | | 2:0 (1:0) |
| Barnsley |
Football League Cup 1995/96, Second round |
| 03.10.1995 | | Barnsley | – | Huddersfield Town | | 4:0 (1:0) |
| Barnsley |
Football League Cup 1991/92, Second round |
| 08.10.1991 | | Barnsley | – | Blackpool | | 2:0 aet |
| Barnsley |
Football League Cup 1990/91, First Round |
| 28.08.1990 | | Wigan Athletic | – | Barnsley | | 0:1 |
| Wigan |
Football League Cup 1988/89, Second round |
| 12.10.1988 | | Wimbledon | – | Barnsley | | 0:1 |
| London |
Football League Cup 1987/88, Second round |
| 06.10.1987 | | West Ham United | – | Barnsley | | 2:5 aet |
| London |
Football League Cup 1982/83, Third round |
| 09.11.1982 | | Sheffield United | – | Barnsley | | 1:3 |
| |
Football League Cup 1982/83, Second round |
| 26.10.1982 | | Cambridge United | – | Barnsley | | 1:3 |
| |
Football League Cup 1982/83, Second round |
| 12.10.1982 | | Barnsley | – | Cambridge United | | 2:1 |
| |
Football League Cup 1981/82, Fourth Round |
| 02.12.1981 | | Barnsley | – | Manchester City | | 1:0 |
| |
Football League Cup 1981/82, Third round |
| 10.11.1981 | | Barnsley | – | Brighton & Hove Albion | | 4:1 |
| |
Football League Cup 1981/82, Second round |
| 06.10.1981 | | Barnsley | – | Swansea City |  | 2:0 |
| |
Football League Cup 1981/82, First Round |
| 15.09.1981 | | Barnsley | – | Peterborough United | | 6:0 |
| |
Football League Cup 1981/82, First Round |
| 02.09.1981 | | Peterborough United | – | Barnsley | | 2:3 |
| |
Football League Cup 1980/81, Third round |
| 23.09.1980 | | Barnsley | – | Cardiff City | | 3:2 |
| |
Football League Cup 1980/81, Second round |
| 02.09.1980 | | Barnsley | – | Mansfield Town | | 4:2 aet |
| |
Football League Cup 1980/81, First Round |
| 12.08.1980 | | Barnsley | – | Scunthorpe United | | 2:1 |
| |
Football League Cup 1980/81, First Round |
| 09.08.1980 | | Scunthorpe United | – | Barnsley | | 0:1 |
| |
Football League Cup 1979/80, First Round |
| 14.08.1979 | | Barnsley | – | Lincoln City | | 2:1 aet,
pen. 4:3 |
| |
Football League Cup 1977/78, First Round |
| 16.08.1977 | | Barnsley | – | Chesterfield | | 3:0 |
| |
Football League Cup 1976/77, First Round |
| 24.08.1976 | | York City | – | Barnsley | | 1:2 aet * |
| |
Football League Cup 1971/72, First Round |
| 23.08.1971 | | Hartlepool | – | Barnsley | | 0:1 aet * |
| |
Football League Cup 1968/69, First Round |
| 14.08.1968 | | York City | – | Barnsley | | 3:4 |
| |
Football League Cup 1964/65, First Round |
| 02.09.1964 | | Barnsley | – | Lincoln City | | 2:1 |
| |
Football League Cup 1963/64, First Round |
| 11.09.1963 | | Barnsley | – | Darlington | | 6:2 * |
| |
Football League Cup 1962/63, Second round |
| 25.09.1962 | | Barnsley | – | Grimsby Town | | 3:2 |
| |
Football League Cup 1962/63, First Round |
| 13.09.1962 | | Barnsley | – | Hartlepools United | | 2:1 * |
| |
Football League Cup 1961/62, First Round |
| 13.09.1961 | | Barnsley | – | Southport | | 3:2 |
| |
Football League Cup 1960/61, First Round |
| 11.10.1960 | | Ipswich Town | – | Barnsley | | 0:2 |
| |
