| Season |
Competition |
Round Reached |
Date |
Home |
Score |
Away |
| 2011/2012 | F.A. Cup | 4th Qualifying Round Replay | Tue 01 Nov | Hinckley Utd. | 3 - 0 | Darlington |
| Trophy | 1st Round | Sat 10 Dec | Grimsby Town | 3 - 0 | Darlington |
| 2010/2011 | F.A. Cup | 2nd Round | Sat 27 Nov | Darlington | 0 - 2 | York City |
| Trophy | Final | Sat 07 May | Darlington | 1 - 0 | Mansfield Town |
| after extra time, 90 minutes 0-0; played at Wembley |
| 2009/2010 | F.A. Cup | 1st Round | Sat 07 Nov | Barnet | 3 - 1 | Darlington |
| League Cup | 1st Round | Mon 10 Aug | Darlington | 0 - 1 | Leeds Utd. |
| (Associate Members) | Northern 2nd Round | Tue 06 Oct | Leeds Utd. | 2 - 1 | Darlington |
| 2008/2009 | F.A. Cup | 1st Round Replay | Tue 18 Nov | Droylsden | 1 - 0 | Darlington |
| League Cup | 2nd Round | Tue 26 Aug | Watford | 2 - 1 | Darlington |
| after extra time, 90 minutes 1-1 |
| (Associate Members) | Northern Semi-Final | Tue 16 Dec | Rotherham U. | 1 - 1 | Darlington |
| no extra time, Rotherham United won 4-2 on penalties |
| 2007/2008 | F.A. Cup | 1st Round Replay | Tue 20 Nov | Northampton | 2 - 1 | Darlington |
| League Cup | 1st Round | Tue 14 Aug | Barnsley | 2 - 1 | Darlington |
| (Associate Members) | Northern 2nd Round | Tue 09 Oct | Darlington | 0 - 1 | Leeds Utd. |
| 2006/2007 | F.A. Cup | 2nd Round | Sat 02 Dec | Darlington | 1 - 3 | Swansea City |
| League Cup | 2nd Round | Tue 19 Sep | Reading | 3 - 3 | Darlington |
| after extra time, 90 minutes 3-3, Reading won 4-2 on penalties |
| (Associate Members) | Northern Semi-Final | Tue 09 Jan | Doncaster Rvs. | 2 - 0 | Darlington |
| 2005/2006 | F.A. Cup | 1st Round | Sat 05 Nov | Barnsley | 1 - 0 | Darlington |
| League Cup | 1st Round | Tue 23 Aug | Hartlepool U. | 3 - 1 | Darlington |
| (Associate Members) | Northern 1st Round | Tue 18 Oct | Kidderminster | 2 - 1 | Darlington |
| 2004/2005 | F.A. Cup | 1st Round Replay | Tue 23 Nov | Yeovil Town | 1 - 0 | Darlington |
| League Cup | 1st Round | Tue 24 Aug | Darlington | 0 - 2 | Barnsley |
| (Associate Members) | Northern 1st Round | Tue 28 Sep | Mansfield Town | 0 - 0 | Darlington |
| after extra time, 90 minutes 0-0, Mansfield Town won 4-3 on penalties |
| 2003/2004 | F.A. Cup | 1st Round | Sun 09 Nov | AFC Hornchurch | 2 - 0 | Darlington |
| League Cup | 2nd Round | Tue 23 Sep | Wolves | 2 - 0 | Darlington |
| (Associate Members) | Northern 1st Round | Tue 14 Oct | Darlington | 1 - 3 | Hull City |
| 2002/2003 | F.A. Cup | 3rd Round | Sat 04 Jan | Darlington | 2 - 3 | Farnborough T. |
| League Cup | 1st Round | Tue 10 Sep | Huddersfield | 2 - 0 | Darlington |
| (Associate Members) | Northern 1st Round | Tue 22 Oct | Stockport Co. | 1 - 0 | Darlington |
| 2001/2002 | F.A. Cup | 3rd Round Replay | Mon 21 Jan | Peterborough | 2 - 0 | Darlington |
| League Cup | 1st Round | Mon 20 Aug | Darlington | 0 - 1 | Sheff. Utd. |
| (Associate Members) | Northern 2nd Round | Tue 30 Oct | Scunthorpe U. | 3 - 0 | Darlington |
| 2000/2001 | F.A. Cup | 2nd Round Replay | Tue 19 Dec | Luton Town | 2 - 0 | Darlington |
| League Cup | 2nd Round | Mon 25 Sep | Bradford City | 7 - 2 | Darlington |
| (Associate Members) | Northern Quarter-Final | Tue 06 Feb | Port Vale | 4 - 0 | Darlington |
| 1999/2000 | F.A. Cup | 3rd Round | Sat 11 Dec | Aston Villa | 2 - 1 | Darlington |
| Darlington reinstated in 'lucky loser' draw due to Manchester United's non-participation |
| League Cup | 1st Round | Tue 24 Aug | Bolton Wdrs. | 5 - 3 | Darlington |
| Bolton Wanderers won 6-4 on aggregate |
| (Associate Members) | Northern 1st Round | Tue 07 Dec | Stoke City | 3 - 2 | Darlington |
| after extra time, 90 minutes 2-2, Stoke City won on golden goal rule |
| 1998/1999 | F.A. Cup | 2nd Round Replay | Tue 15 Dec | Man. City | 1 - 0 | Darlington |
| after extra time, 90 minutes 0-0 |
| League Cup | 1st Round | Tue 18 Aug | Darlington | 2 - 2 | Sheff. Utd. |
| after extra time, 90 minutes 2-0, Sheffield United won 5-3 on aggregate |
| (Associate Members) | Northern 2nd Round | Tue 12 Jan | Darlington | 0 - 2 | Chesterfield |
| played at Chesterfield |
| 1997/1998 | F.A. Cup | 3rd Round | Wed 14 Jan | Darlington | 0 - 4 | Wolves |
| League Cup | 1st Round | Tue 26 Aug | Notts. County | 2 - 1 | Darlington |
| after extra time, 90 minutes 1-1, Notts. County won 3-2 on aggregate |
| (Associate Members) | Northern 1st Round | Tue 09 Dec | Preston N.E. | 3 - 2 | Darlington |
| after extra time, 90 minutes 2-2, Preston North End won on golden goal rule |
| 1996/1997 | F.A. Cup | 2nd Round | Sat 07 Dec | Carlisle Utd. | 1 - 0 | Darlington |
| League Cup | 2nd Round | Tue 24 Sep | Darlington | 0 - 2 | Leeds Utd. |
| Leeds United won 4-2 on aggregate |
| (Associate Members) | Northern 1st Round | Tue 10 Dec | Bury | 3 - 1 | Darlington |
| 1995/1996 | F.A. Cup | 2nd Round Replay | Tue 12 Dec | Darlington | 0 - 1 | Rochdale |
| League Cup | 1st Round | Tue 05 Sep | Darlington | 1 - 1 | Crewe Alex. |
| Crewe Alexandra won 5-1 on aggregate |
| (Associate Members) | Northern Preliminary Round Group Four | Tue 07 Nov | Darlington | 0 - 1 | Lincoln City |
| 1994/1995 | F.A. Cup | 2nd Round | Sun 04 Dec | Carlisle Utd. | 2 - 0 | Darlington |
| League Cup | 1st Round | Tue 23 Aug | Barnsley | 0 - 0 | Darlington |
| after extra time, 90 minutes 0-0, aggregate 2-2, Barnsley won on away goals rule |
| (Associate Members) | Northern 1st Round | Tue 29 Nov | Rochdale | 2 - 2 | Darlington |
| after extra time, 90 minutes 2-2, Rochdale won 4-3 on penalties |
| 1993/1994 | F.A. Cup | 1st Round | Sat 13 Nov | Crewe Alex. | 4 - 2 | Darlington |
| League Cup | 1st Round | Wed 25 Aug | Bradford City | 6 - 0 | Darlington |
| Bradford City won 11-1 on aggregate |
| (Associate Members) | Northern 1st Round | Tue 30 Nov | Lincoln City | 3 - 2 | Darlington |
| 1992/1993 | F.A. Cup | 1st Round | Sat 14 Nov | Darlington | 1 - 2 | Hull City |
| League Cup | 1st Round | Tue 25 Aug | Scunthorpe U. | 2 - 0 | Darlington |
| Scunthorpe United won 3-1 on aggregate |
| (Associate Members) | Northern 1st Round | Mon 18 Jan | Darlington | 3 - 4 | Bolton Wdrs. |
| after extra-time, 90 minutes 3-3 |
| 1991/1992 | F.A. Cup | 2nd Round | Tue 17 Dec | Darlington | 1 - 2 | Hartlepool U. |
| League Cup | 1st Round | Tue 27 Aug | Huddersfield | 4 - 0 | Darlington |
| Huddersfield Town won 4-1 on aggregate |
| (Associate Members) | Northern Preliminary Round Group Three | Tue 07 Jan | Chester City | 2 - 1 | Darlington |
| 1990/1991 | F.A. Cup | 1st Round Replay | Mon 19 Nov | York City | 1 - 0 | Darlington |
| League Cup | 2nd Round | Tue 09 Oct | Swindon Town | 4 - 0 | Darlington |
| Swindon Town won 4-3 on aggregate |
| (Associate Members) | Northern 1st Round | Tue 08 Jan | Preston N.E. | 2 - 1 | Darlington |
| after extra time, 90 minutes 1-1 |
| 1989/1990 | F.A. Cup | 3rd Round Replay | Tue 09 Jan | Darlington | 1 - 3 | Cambridge U. |
| 1988/1989 | F.A. Cup | 1st Round | Sat 19 Nov | Darlington | 1 - 2 | Notts. County |
| League Cup | 2nd Round | Tue 11 Oct | Oldham Ath. | 4 - 0 | Darlington |
| Oldham Athletic won 4-2 on aggregate |
| (Associate Members) | Northern 1st Round | Tue 17 Jan | Halifax Town | 3 - 0 | Darlington |
| 1987/1988 | F.A. Cup | 1st Round | Sat 14 Nov | Sunderland | 2 - 0 | Darlington |
| League Cup | 2nd Round | Tue 06 Oct | Watford | 8 - 0 | Darlington |
| Watford won 11-0 on aggregate |
| (Associate Members) | Northern Quarter-Final | Thu 18 Feb | Darlington | 1 - 2 | Halifax Town |
| 1986/1987 | F.A. Cup | 2nd Round | Sat 06 Dec | Darlington | 0 - 5 | Wigan Ath. |
| League Cup | 1st Round | Tue 02 Sep | Darlington | 1 - 2 | Scunthorpe U. |
| Scunthorpe United won 4-1 on aggregate |
| (Associate Members) | Northern Preliminary Round Group Eight | Tue 02 Dec | Darlington | 2 - 2 | Rochdale |
