| Season |
Competition |
Round Reached |
Date |
Home |
Score |
Away |
| 2006/2007 | Trophy | 1st Round | Sat 16 Dec | Rushden & D. | 3 - 2 | Scarborough |
| 2005/2006 | Trophy | 1st Round | Sat 17 Dec | Kidderminster | 4 - 0 | Scarborough |
| 2004/2005 | F.A. Cup | 4th Qualifying Round Replay | Tue 02 Nov | Scarborough | 0 - 1 | Lancaster C. |
| (Associate Members) | Northern 1st Round | Tue 28 Sep | Rochdale | 4 - 1 | Scarborough |
| Trophy | 3rd Round | Sat 15 Jan | Barrow | 2 - 1 | Scarborough |
| 2003/2004 | F.A. Cup | 4th Round | Sat 24 Jan | Scarborough | 0 - 1 | Chelsea |
| (Associate Members) | Northern 2nd Round | Tue 04 Nov | Scarborough | 0 - 1 | Halifax Town |
| Trophy | 3rd Round | Sat 10 Jan | Scarborough | 1 - 2 | Stafford Rgrs. |
| 2002/2003 | F.A. Cup | 1st Round Replay | Tue 26 Nov | Cambridge U. | 2 - 1 | Scarborough |
| after extra time, 90 minutes 1-1 |
| (Associate Members) | Northern 1st Round | Tue 22 Oct | Scarborough | 1 - 2 | Doncaster Rvs. |
| after extra time, 90 minutes 1-1, Doncaster Rovers won on the golden goal rule |
| Trophy | 4th Round Replay | Mon 17 Feb | Dover Ath. | 2 - 1 | Scarborough |
| after extra time, 90 minutes 1-1 |
| 2001/2002 | (Associate Members) | Northern 1st Round | Tue 16 Oct | Leigh Genesis | 2 - 1 | Scarborough |
| after extra time, 90 minutes 1-1, Leigh RMI won on the golden goal rule |
| Trophy | 5th Round Replay | Tue 26 Feb | Morecambe | 3 - 0 | Scarborough |
| 2000/2001 | F.A. Cup | 4th Qualifying Round | Sat 28 Oct | Scarborough | 3 - 4 | Leigh Genesis |
| (Associate Members) | Northern 1st Round | Wed 06 Dec | Stoke City | 3 - 0 | Scarborough |
| Trophy | 4th Round | Sat 03 Feb | Scarborough | 0 - 1 | Burton Albion |
| 1998/1999 | F.A. Cup | 1st Round Replay | Tue 24 Nov | Rochdale | 2 - 0 | Scarborough |
| League Cup | 1st Round | Tue 18 Aug | Barnsley | 3 - 0 | Scarborough |
| Barnsley won 4-0 on aggregate |
| (Associate Members) | Northern 2nd Round | Tue 19 Jan | Wigan Ath. | 3 - 0 | Scarborough |
| 1997/1998 | F.A. Cup | 1st Round | Sat 15 Nov | Scunthorpe U. | 2 - 1 | Scarborough |
| League Cup | 1st Round | Tue 26 Aug | Scunthorpe U. | 2 - 1 | Scarborough |
| Scunthorpe United won 4-1 on aggregate |
| (Associate Members) | Northern 1st Round | Tue 09 Dec | Hull City | 2 - 1 | Scarborough |
| 1996/1997 | F.A. Cup | 2nd Round | Sat 07 Dec | Chesterfield | 2 - 0 | Scarborough |
| League Cup | 2nd Round | Wed 25 Sep | Leicester City | 2 - 1 | Scarborough |
| Leicester City won 4-1 on aggregate |
| (Associate Members) | Northern 1st Round | Tue 10 Dec | Scarborough | 0 - 1 | Notts. County |
| 1995/1996 | F.A. Cup | 1st Round | Sat 11 Nov | Scarborough | 0 - 2 | Chesterfield |
| League Cup | 1st Round | Tue 22 Aug | Hartlepool U. | 1 - 0 | Scarborough |
| after extra time, 90 minutes 1-0, aggregate 1-1, Hartlepool United won 7-6 on penalties |
| (Associate Members) | Northern Preliminary Round Group Seven | Tue 07 Nov | Preston N.E. | 2 - 1 | Scarborough |
| 1994/1995 | F.A. Cup | 3rd Round Replay | Tue 17 Jan | Watford | 2 - 0 | Scarborough |
| League Cup | 2nd Round | Tue 27 Sep | Middlesbrough | 4 - 1 | Scarborough |
| Middlesbrough won 8-2 on aggregate |
| (Associate Members) | Northern 1st Round | Tue 29 Nov | Stockport Co. | 3 - 1 | Scarborough |
| 1993/1994 | F.A. Cup | 2nd Round | Sat 04 Dec | Wigan Ath. | 1 - 0 | Scarborough |
| League Cup | 1st Round | Tue 24 Aug | Scarborough | 0 - 3 | Huddersfield |
| Huddersfield Town won 3-0 on aggregate |
| (Associate Members) | Northern 1st Round | Wed 01 Dec | Scarborough | 0 - 2 | Scunthorpe U. |
| 1992/1993 | F.A. Cup | 1st Round | Sat 14 Nov | Burnley | 2 - 1 | Scarborough |
| League Cup | 4th Round | Wed 06 Jan | Scarborough | 0 - 1 | Arsenal |
| (Associate Members) | Northern 1st Round | Tue 12 Jan | Scarborough | 3 - 4 | Bradford City |
| 1991/1992 | F.A. Cup | 1st Round | Sat 16 Nov | Scarborough | 0 - 2 | Wigan Ath. |
| League Cup | 2nd Round | Wed 09 Oct | Southampton | 2 - 2 | Scarborough |
| Southampton won 5-3 on aggregate |
| (Associate Members) | Northern 1st Round | Tue 04 Feb | Burnley | 3 - 1 | Scarborough |
| 1990/1991 | F.A. Cup | 1st Round | Sat 17 Nov | Scarborough | 0 - 2 | Leek |
| League Cup | 1st Round | Wed 05 Sep | Scarborough | 3 - 3 | Rochdale |
| Rochdale won 7-3 on aggregate |
| (Associate Members) | Northern Preliminary Round Group One | Wed 09 Jan | Scarborough | 1 - 2 | Halifax Town |
| 1989/1990 | F.A. Cup | 1st Round | Sat 18 Nov | Scarborough | 0 - 1 | Whitley Bay |
| League Cup | 3rd Round | Wed 25 Oct | Oldham Ath. | 7 - 0 | Scarborough |
| (Associate Members) | Northern Preliminary Round Group Seven | Wed 29 Nov | Scarborough | 0 - 1 | Carlisle Utd. |
| 1988/1989 | F.A. Cup | 2nd Round | Sat 10 Dec | Scarborough | 0 - 1 | Carlisle Utd. |
| League Cup | 3rd Round Replay | Tue 22 Nov | Southampton | 1 - 0 | Scarborough |
| (Associate Members) | Northern Semi-Final | Tue 21 Mar | Blackpool | 1 - 0 | Scarborough |
| after extra time, 90 minutes 0-0 |
| 1987/1988 | F.A. Cup | 1st Round | Sat 14 Nov | Scarborough | 1 - 2 | Grimsby Town |
| League Cup | 1st Round | Tue 25 Aug | Doncaster Rvs. | 3 - 1 | Scarborough |
| Doncaster Rovers won 3-2 on aggregate |
| (Associate Members) | Northern Preliminary Round Group Six | Wed 28 Oct | Scarborough | 0 - 3 | Sunderland |
