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, First Round |
| 26.08.1997 | | Scunthorpe United | – | Scarborough | | 2:1 (1:1) |
| Scunthorpe |
Football League Cup 1997/98, First Round |
| 12.08.1997 | | Scarborough | – | Scunthorpe United | | 0:2 (0:1) |
| Scarborough |
Football League Cup 1996/97, Second round |
| 25.09.1996 | | Leicester City | – | Scarborough | | 2:1 (1:0) |
| Leicester |
Football League Cup 1996/97, Second round |
| 17.09.1996 | | Scarborough | – | Leicester City | | 0:2 (0:1) |
| Scarborough |
Football League Cup 1996/97, First Round |
| 03.09.1996 | | Scarborough | – | Hull City | | 3:2 (2:0) |
| Scarborough |
Football League Cup 1996/97, First Round |
| 20.08.1996 | | Hull City | – | Scarborough | | 2:2 (1:1) |
| Kingston upon Hull |
Football League Cup 1995/96, First Round |
| 22.08.1995 | | Hartlepool United | – | Scarborough | | 1:0 aet,
pen. 7:6 |
| Hartlepool |
Football League Cup 1995/96, First Round |
| 15.08.1995 | | Scarborough | – | Hartlepool United | | 1:0 (0:0) |
| Scarborough |
Football League Cup 1994/95, Second round |
| 27.09.1994 | | Middlesbrough | – | Scarborough | | 4:1 (1:1) |
| Middlesbrough |
Football League Cup 1994/95, Second round |
| 20.09.1994 | | Scarborough | – | Middlesbrough | | 1:4 (1:4) |
| Scarborough |
Football League Cup 1994/95, First Round |
| 07.09.1994 | | Scarborough | – | Hull City | | 2:0 (1:0) |
| Scarborough |
Football League Cup 1994/95, First Round |
| 16.08.1994 | | Hull City | – | Scarborough | | 2:1 (1:0) |
| Kingston upon Hull |
Football League Cup 1993/94, First Round |
| 24.08.1993 | | Scarborough | – | Huddersfield Town | | 0:3 (0:1) |
| Scarborough |
Football League Cup 1993/94, First Round |
| 17.08.1993 | | Huddersfield Town | – | Scarborough | | 0:0 |
| Huddersfield |
Football League Cup 1992/93, Fourth Round |
| 06.01.1993 | | Scarborough | – | Arsenal | | 0:3 (0:1) |
| Scarborough |
Football League Cup 1992/93, Third round |
| 11.11.1992 | | Scarborough | – | Plymouth Argyle | | 2:1 (0:1) * |
| Scarborough |
Football League Cup 1992/93, Third round |
| 27.10.1992 | | Plymouth Argyle | – | Scarborough | | 3:3 (0:1) |
| Plymouth |
Football League Cup 1992/93, Second round |
| 07.10.1992 | | Scarborough | – | Coventry City | | 3:0 (0:0) |
| Scarborough |
Football League Cup 1992/93, Second round |
| 23.09.1992 | | Coventry City | – | Scarborough | | 2:0 (0:0) |
| Coventry |
Football League Cup 1992/93, First Round |
| 26.08.1992 | | Bradford City | – | Scarborough | | 3:5 (2:3) |
| Bradford |
Football League Cup 1992/93, First Round |
| 19.08.1992 | | Scarborough | – | Bradford City | | 3:0 (2:0) |
| Scarborough |
Football League Cup 1991/92, Second round |
| 09.10.1991 | | Southampton | – | Scarborough | | 2:2 (2:0) |
| Southampton |
Football League Cup 1991/92, Second round |
| 24.09.1991 | | Scarborough | – | Southampton | | 1:3 (1:2) |
| Scarborough |
Football League Cup 1991/92, First Round |
| 28.08.1991 | | Scarborough | – | Preston North End | | 3:1 aet |
| Scarborough |
Football League Cup 1991/92, First Round |
| 20.08.1991 | | Preston North End | – | Scarborough | | 5:4 (2:2) |
| Preston |
Football League Cup 1990/91, First Round |
| 05.09.1990 | | Scarborough | – | Rochdale | | 3:3 |
| Scarborough |
Football League Cup 1990/91, First Round |
| 28.08.1990 | | Rochdale | – | Scarborough | | 4:0 |
| Rochdale |
Football League Cup 1989/90, Third round |
| 25.10.1989 | | Oldham Athletic | – | Scarborough | | 7:0 |
| Oldham |
Football League Cup 1989/90, Second round |
| 04.10.1989 | | Scarborough | – | Chelsea | | 3:2 aet |
| Scarborough |
Football League Cup 1989/90, Second round |
| 19.09.1989 | | Chelsea | – | Scarborough | | 1:1 |
| London |
Football League Cup 1989/90, First Round |
| 29.08.1989 | | Scunthorpe United | – | Scarborough | | 1:1 |
| Scunthorpe |
Football League Cup 1989/90, First Round |
| 22.08.1989 | | Scarborough | – | Scunthorpe United | | 2:0 |
| Scarborough |
Football League Cup 1988/89, Third round |
| 22.11.1988 | | Southampton | – | Scarborough | | 1:0 * |
| Southampton |
Football League Cup 1988/89, Third round |
| 02.11.1988 | | Scarborough | – | Southampton | | 2:2 |
| Scarborough |
Football League Cup 1988/89, Second round |
| 12.10.1988 | | Scarborough | – | Portsmouth | | 3:1 |
| Scarborough |
Football League Cup 1988/89, Second round |
| 27.09.1988 | | Portsmouth | – | Scarborough | | 2:2 |
| Portsmouth |
Football League Cup 1988/89, First Round |
| 06.09.1988 | | Halifax Town | – | Scarborough | | 2:2 aet |
| Halifax |
Football League Cup 1988/89, First Round |
| 31.08.1988 | | Scarborough | – | Halifax Town | | 1:1 |
| Scarborough |
Football League Cup 1987/88, First Round |
| 25.08.1987 | | Doncaster Rovers | – | Scarborough | | 3:1 |
| Doncaster |
Football League Cup 1987/88, First Round |
| 19.08.1987 | | Scarborough | – | Doncaster Rovers | | 1:0 |
| Scarborough |
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