| Season |
Competition |
Round Reached |
Date |
Home |
Score |
Away |
| 2012/2013 | F.A. Cup | 1st Round Replay | Mon 12 Nov | AFC Wimbledon | 4 - 3 | York City |
| after extra time, 90 minutes 2-2 |
| League Cup | 1st Round | Sat 11 Aug | Doncaster Rvs. | 1 - 1 | York City |
| after extra time, 90 minutes 1-1, Doncaster Rovers won 4-2 on penalties |
| (Associate Members) | Northern 2nd Round | Tue 09 Oct | York City | 0 - 4 | Coventry City |
| 2011/2012 | F.A. Cup | 4th Qualifying Round | Sat 29 Oct | Wrexham | 2 - 1 | York City |
| Trophy | Final | Sat 12 May | Newport Co. | 0 - 2 | York City |
| played at Wembley |
| 2010/2011 | F.A. Cup | 3rd Round | Sat 08 Jan | Bolton Wdrs. | 2 - 0 | York City |
| Trophy | 1st Round | Sat 11 Dec | York City | 0 - 1 | Boston Utd. |
| 2009/2010 | F.A. Cup | 3rd Round | Sat 02 Jan | Stoke City | 3 - 1 | York City |
| Trophy | 4th Round | Tue 02 Mar | Barrow | 2 - 1 | York City |
| 2008/2009 | Trophy | Final | Sat 09 May | Stevenage B. | 2 - 0 | York City |
| played at Wembley |
| 2007/2008 | F.A. Cup | 1st Round | Sat 10 Nov | York City | 0 - 1 | Havant & W. |
| Trophy | Semi Final | Sat 15 Mar | York City | 1 - 0 | Torquay Utd. |
| Torquay United won 2-1 on aggregate |
| 2006/2007 | F.A. Cup | 1st Round | Sat 11 Nov | York City | 0 - 1 | Bristol City |
| Trophy | 1st Round | Sat 16 Dec | Morecambe | 2 - 1 | York City |
| 2005/2006 | F.A. Cup | 1st Round | Sat 05 Nov | York City | 0 - 3 | Grays Ath. |
| Trophy | 1st Round | Sat 17 Dec | York City | 1 - 2 | Northwich Vic. |
| 2004/2005 | F.A. Cup | 4th Qualifying Round | Sat 30 Oct | Carlisle Utd. | 3 - 1 | York City |
| (Associate Members) | Northern 1st Round | Wed 29 Sep | York City | 0 - 2 | Blackpool |
| Trophy | 3rd Round | Sat 15 Jan | Burton Albion | 3 - 0 | York City |
| 2003/2004 | F.A. Cup | 1st Round | Sun 09 Nov | York City | 1 - 2 | Barnsley |
| League Cup | 1st Round | Tue 12 Aug | Rotherham U. | 2 - 1 | York City |
| (Associate Members) | Northern 1st Round | Tue 14 Oct | Halifax Town | 2 - 1 | York City |
| 2002/2003 | F.A. Cup | 2nd Round | Sat 07 Dec | York City | 1 - 2 | Brentford |
| League Cup | 1st Round | Tue 10 Sep | Sheff. Utd. | 1 - 0 | York City |
| (Associate Members) | Northern 1st Round | Tue 22 Oct | Lincoln City | 4 - 3 | York City |
| 2001/2002 | F.A. Cup | 4th Round | Sat 26 Jan | York City | 0 - 2 | Fulham |
| League Cup | 1st Round | Tue 21 Aug | York City | 2 - 2 | Crewe Alex. |
| after extra time, 90 minutes 1-1, Crewe Alexandra won 6-5 on penalties |
| (Associate Members) | Northern 1st Round | Tue 16 Oct | Notts. County | 2 - 0 | York City |
| 2000/2001 | F.A. Cup | 3rd Round | Sat 06 Jan | Leicester City | 3 - 0 | York City |
| League Cup | 1st Round | Wed 06 Sep | Stoke City | 0 - 0 | York City |
| (Associate Members) | Northern 1st Round | Tue 09 Jan | York City | 0 - 4 | Darlington |
| 1999/2000 | F.A. Cup | 1st Round | Sat 30 Oct | Hereford Utd. | 1 - 0 | York City |
| League Cup | 1st Round | Tue 24 Aug | Wigan Ath. | 2 - 1 | York City |
| Wigan Athletic won 3-1 on aggregate |
| (Associate Members) | Northern 1st Round | Tue 07 Dec | York City | 0 - 1 | Hull City |
| 1998/1999 | F.A. Cup | 2nd Round | Sat 05 Dec | Wrexham | 2 - 1 | York City |
| League Cup | 1st Round | Tue 18 Aug | Sunderland | 2 - 1 | York City |
| Sunderland won 4-1 on aggregate |
| (Associate Members) | Northern 2nd Round | Tue 05 Jan | Halifax Town | 4 - 2 | York City |
| 1997/1998 | F.A. Cup | 2nd Round | Sat 06 Dec | Wigan Ath. | 2 - 1 | York City |
| League Cup | 2nd Round | Tue 23 Sep | York City | 1 - 2 | Oxford Utd. |
| Oxford United won 6-2 on aggregate |
| (Associate Members) | Northern 2nd Round | Tue 06 Jan | Blackpool | 1 - 1 | York City |
| after extra time, 90 minutes 1-1, Blackpool won 10-9 on penalties |
| 1996/1997 | F.A. Cup | 3rd Round | Mon 13 Jan | Hednesford T. | 1 - 0 | York City |
| League Cup | 3rd Round | Tue 22 Oct | York City | 0 - 2 | Leicester City |
| (Associate Members) | Northern Quarter-Final | Tue 04 Feb | York City | 0 - 2 | Carlisle Utd. |
| 1995/1996 | F.A. Cup | 1st Round | Sun 12 Nov | York City | 0 - 1 | Notts. County |
| League Cup | 3rd Round | Wed 25 Oct | Q.P.R. | 3 - 1 | York City |
| (Associate Members) | Northern Semi-Final | Tue 13 Feb | Rotherham U. | 4 - 1 | York City |
| 1994/1995 | F.A. Cup | 1st Round Replay | Tue 22 Nov | Rotherham U. | 3 - 0 | York City |
| League Cup | 1st Round | Tue 23 Aug | York City | 2 - 2 | Burnley |
| Burnley won 3-2 on aggregate |
| (Associate Members) | Northern Preliminary Round Group Seven | Tue 08 Nov | York City | 2 - 2 | Bradford City |
| 1993/1994 | F.A. Cup | 1st Round Replay | Tue 30 Nov | York City | 2 - 3 | Burnley |
| League Cup | 1st Round | Tue 24 Aug | York City | 0 - 0 | Rochdale |
| Rochdale won 2-0 on aggregate |
| (Associate Members) | Northern 1st Round | Sat 04 Dec | York City | 1 - 1 | Mansfield Town |
| after extra time, 90 minutes 1-1, Mansfield Town won 5-4 on penalties |
| 1992/1993 | F.A. Cup | 1st Round | Sat 14 Nov | York City | 1 - 3 | Stockport Co. |
| League Cup | 1st Round | Tue 25 Aug | York City | 0 - 0 | Chesterfield |
| Chesterfield won 2-0 on aggregate |
| (Associate Members) | Northern Preliminary Round Group One | Tue 08 Dec | York City | 0 - 0 | Hull City |
| 1991/1992 | F.A. Cup | 2nd Round Replay | Tue 17 Dec | Tranmere Rvs. | 2 - 1 | York City |
| League Cup | 1st Round | Tue 27 Aug | York City | 1 - 2 | Bolton Wdrs. |
| Bolton Wanderers won 4-3 on aggregate |
| (Associate Members) | Northern Preliminary Round Group Seven | Tue 07 Jan | Stockport Co. | 3 - 0 | York City |
| 1990/1991 | F.A. Cup | 2nd Round | Mon 17 Dec | Mansfield Town | 2 - 1 | York City |
| League Cup | 1st Round | Tue 04 Sep | Wrexham | 2 - 0 | York City |
| Wrexham won 3-0 on aggregate |
| (Associate Members) | Northern 1st Round | Tue 22 Jan | York City | 1 - 2 | Bury |
| 1989/1990 | F.A. Cup | 1st Round | Sat 18 Nov | York City | 1 - 2 | Grimsby Town |
| League Cup | 2nd Round | Tue 03 Oct | Southampton | 2 - 0 | York City |
| Southampton won 3-0 on aggregate |
| (Associate Members) | Northern 1st Round | Tue 09 Jan | Halifax Town | 1 - 1 | York City |
| after extra time, 90 minutes 0-0, Halifax Town won 7-6 on penalties |
| 1988/1989 | F.A. Cup | 1st Round | Sat 19 Nov | Halifax Town | 1 - 0 | York City |
| League Cup | 1st Round | Tue 06 Sep | Sunderland | 4 - 0 | York City |
| Sunderland won 4-0 on aggregate |
| (Associate Members) | Northern 1st Round | Sat 07 Jan | Scarborough | 3 - 1 | York City |
| 1987/1988 | F.A. Cup | 2nd Round Replay | Wed 09 Dec | Hartlepool U. | 3 - 1 | York City |
| League Cup | 2nd Round | Tue 06 Oct | York City | 0 - 4 | Leeds Utd. |
| Leeds United won 5-1 on aggregate |
| (Associate Members) | Northern Preliminary Round Group Five | Tue 24 Nov | Chesterfield | 2 - 0 | York City |
| 1986/1987 | F.A. Cup | 2nd Round Replay | Tue 09 Dec | York City | 1 - 2 | Caernarfon T. |
| League Cup | 2nd Round | Wed 08 Oct | Chelsea | 3 - 0 | York City |
| Chelsea won 3-1 on aggregate |
| (Associate Members) | Northern 1st Round | Tue 27 Jan | York City | 0 - 1 | Mansfield Town |
