| Season |
Competition |
Round Reached |
Date |
Home |
|
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 Section 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 Section 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 Section 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 Section 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 Section 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 Section 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 | Hornchurch | 2 - 0 | Darlington |
| League Cup | 2nd Round | Tue 23 Sep | Wolves | 2 - 0 | Darlington |
| (Associate Members) | Northern Section 1st Round | Tue 14 Oct | Darlington | 1 - 3 | Hull City |
| 2002/2003 | F.A. Cup | 3rd Round | Sat 04 Jan | Darlington | 2 - 3 | Farnborough Town |
| League Cup | 1st Round | Tue 10 Sep | Huddersfield | 2 - 0 | Darlington |
| (Associate Members) | Northern Section 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 Section 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 Section 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 Section 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 Section 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 Section 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 Section 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 Section 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 Section 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 Section 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 Section 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 Section 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 Section 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 Section 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 Section 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 Section Preliminary Round Group Eight | Tue 02 Dec | Darlington | 2 - 2 | Rochdale |
| 1985/1986 | F.A. Cup | 1st Round | Sat 16 Nov | Rochdale | 2 - 1 | Darlington |
| League Cup | 2nd Round | Tue 08 Oct | Darlington | 1 - 4 | Ipswich Town |
| Ipswich Town won 7-2 on aggregate |
| (Associate Members) | Northern Section Semi-Final | Thu 01 May | Darlington | 0 - 3 | Bolton Wdrs. |
| 1984/1985 | F.A. Cup | 4th Round Replay | Mon 04 Feb | Telford Utd. | 3 - 0 | Darlington |
| League Cup | 1st Round | Tue 04 Sep | Rotherham U. | 4 - 0 | Darlington |
| Rotherham United won 6-1 on aggregate |
| (Associate Members) | Northern Section Quarter-Final | Tue 16 Apr | Bolton Wdrs. | 2 - 1 | Darlington |
| 1983/1984 | F.A. Cup | 4th Round | Sat 28 Jan | Plymouth Arg. | 2 - 1 | Darlington |
| League Cup | 2nd Round | Tue 25 Oct | Darlington | 2 - 4 | Sheff. Wed. |
| Sheffield Wednesday won 7-2 on aggregate |
| (Associate Members) | Northern Section 2nd Round | Tue 13 Mar | Burnley | 2 - 1 | Darlington |
| 1982/1983 | F.A. Cup | 1st Round | Sat 20 Nov | Darlington | 0 - 1 | Scunthorpe U. |
| League Cup | 1st Round | Wed 15 Sep | Peterborough | 4 - 2 | Darlington |
| Peterborough United won 6-2 on aggregate |
| 1981/1982 | F.A. Cup | 1st Round Replay | Tue 24 Nov | Carlisle Utd. | 3 - 1 | Darlington |
| League Cup | 1st Round | Tue 15 Sep | Rotherham U. | 2 - 1 | Darlington |
| Rotherham United won 5-2 on aggregate |
| 1980/1981 | F.A. Cup | 1st Round | Sat 22 Nov | Darlington | 0 - 2 | Bury |
| League Cup | 1st Round | Tue 12 Aug | Darlington | 1 - 2 | Chesterfield |
| Chesterfield won 3-1 on aggregate |
| 1979/1980 | F.A. Cup | 2nd Round | Sat 15 Dec | Darlington | 0 - 1 | Bradford City |
| League Cup | 1st Round | Tue 14 Aug | Darlington | 0 - 3 | Bradford City |
| Bradford City won 3-2 on aggregate |
| 1978/1979 | F.A. Cup | 3rd Round | Tue 09 Jan | Darlington | 0 - 1 | Colchester U. |
| League Cup | 3rd Round | Tue 03 Oct | Everton | 1 - 0 | Darlington |
| 1977/1978 | F.A. Cup | 1st Round | Sat 26 Nov | Chester | 4 - 1 | Darlington |
| League Cup | 1st Round | Tue 16 Aug | Scunthorpe U. | 3 - 1 | Darlington |
| Scunthorpe United won 3-1 on aggregate |
| 1976/1977 | F.A. Cup | 3rd Round 2nd Replay | Mon 17 Jan | Orient | 3 - 0 | Darlington |
| played at neutral ground |
| League Cup | 2nd Round | Wed 01 Sep | Bury | 2 - 1 | Darlington |
| 1975/1976 | F.A. Cup | 1st Round Replay | Wed 26 Nov | Chester | 2 - 0 | Darlington |
| League Cup | 3rd Round | Wed 08 Oct | West Ham Utd. | 3 - 0 | Darlington |
| 1974/1975 | F.A. Cup | 2nd Round | Sat 14 Dec | Blackburn R. | 1 - 0 | Darlington |
| League Cup | 1st Round | Tue 20 Aug | Bradford City | 2 - 1 | Darlington |
| 1973/1974 | F.A. Cup | 1st Round | Sat 24 Nov | Scunthorpe U. | 1 - 0 | Darlington |
| League Cup | 2nd Round | Mon 08 Oct | Coventry City | 5 - 1 | Darlington |
| 1972/1973 | F.A. Cup | 1st Round Replay | Wed 22 Nov | Wrexham | 5 - 0 | Darlington |
| League Cup | 1st Round | Wed 16 Aug | Darlington | 0 - 1 | Rotherham U. |
| 1971/1972 | F.A. Cup | 2nd Round | Sat 11 Dec | Port Vale | 1 - 0 | Darlington |
| League Cup | 1st Round | Wed 18 Aug | Darlington | 0 - 1 | York City |
| 1970/1971 | F.A. Cup | 2nd Round | Sat 12 Dec | Darlington | 0 - 2 | Rochdale |
| League Cup | 2nd Round | Wed 09 Sep | Darlington | 0 - 4 | Fulham |
| 1969/1970 | F.A. Cup | 1st Round Replay | Tue 18 Nov | Barnsley | 2 - 0 | Darlington |
| League Cup | 2nd Round | Wed 03 Sep | Darlington | 0 - 1 | Everton |
| 1968/1969 | F.A. Cup | 2nd Round Replay | Tue 10 Dec | Barnsley | 1 - 0 | Darlington |
| after extra time, 90 minutes 0-0 |
| League Cup | 2nd Round | Wed 04 Sep | Darlington | 1 - 2 | Leicester City |
| 1967/1968 | F.A. Cup | 1st Round | Wed 13 Dec | Shrewsbury Tn. | 3 - 0 | Darlington |
| League Cup | Quarter Final | Wed 29 Nov | Derby County | 5 - 4 | Darlington |
| 1966/1967 | F.A. Cup | 2nd Round | Sat 07 Jan | Crewe Alex. | 2 - 1 | Darlington |
| League Cup | 2nd Round Replay | Mon 19 Sep | Doncaster Rvs. | 2 - 0 | Darlington |
| 1965/1966 | F.A. Cup | 2nd Round | Sat 04 Dec | Darlington | 0 - 1 | Oldham Ath. |
| League Cup | 4th Round | Wed 03 Nov | Ipswich Town | 2 - 0 | Darlington |
| 1964/1965 | F.A. Cup | 3rd Round | Sat 09 Jan | Darlington | 0 - 2 | Arsenal |
| League Cup | 2nd Round | Wed 23 Sep | Bury | 1 - 0 | Darlington |
| 1963/1964 | F.A. Cup | 1st Round | Sat 16 Nov | Darlington | 1 - 4 | Gateshead |
| League Cup | 1st Round Replay | Wed 11 Sep | Barnsley | 6 - 2 | Darlington |
| 1962/1963 | F.A. Cup | 1st Round Replay | Wed 07 Nov | Darlington | 1 - 2 | Lincoln City |
| League Cup | 2nd Round | Tue 25 Sep | Swindon Town | 4 - 0 | Darlington |
| 1961/1962 | F.A. Cup | 1st Round | Sat 04 Nov | Darlington | 0 - 4 | Carlisle Utd. |
| League Cup | 1st Round | Mon 11 Sep | Darlington | 0 - 1 | Rotherham U. |
| 1960/1961 | F.A. Cup | 2nd Round 3rd Replay | Thu 15 Dec | Hull City | 3 - 0 | Darlington |
| played at neutral ground |
| League Cup | 3rd Round | Mon 14 Nov | Darlington | 1 - 2 | Bolton Wdrs. |
| 1959/1960 | F.A. Cup | 2nd Round | Sat 05 Dec | Doncaster Rvs. | 3 - 2 | Darlington |
| 1958/1959 | F.A. Cup | 3rd Round | Sat 10 Jan | Accrington S. | 3 - 0 | Darlington |
| 1957/1958 | F.A. Cup | 5th Round | Sat 15 Feb | Wolves | 6 - 1 | Darlington |
| 1956/1957 | F.A. Cup | 2nd Round | Sat 08 Dec | Carlisle Utd. | 2 - 1 | Darlington |
| 1955/1956 | F.A. Cup | 2nd Round | Sat 10 Dec | Darlington | 0 - 1 | Accrington S. |
| 1954/1955 | F.A. Cup | 3rd Round 2nd Replay | Mon 17 Jan | Hartlepools | 2 - 0 | Darlington |
| played at neutral ground |
| 1953/1954 | F.A. Cup | 1st Round | Sat 21 Nov | Darlington | 1 - 3 | Port Vale |
| 1952/1953 | F.A. Cup | 1st Round | Sat 22 Nov | Darlington | 2 - 3 | Grimsby Town |
| 1951/1952 | F.A. Cup | 1st Round | Sat 24 Nov | Grimsby Town | 4 - 0 | Darlington |
| 1950/1951 | F.A. Cup | 1st Round | Sat 25 Nov | Darlington | 2 - 7 | Rotherham U. |
| 1949/1950 | F.A. Cup | 1st Round Replay | Wed 30 Nov | Crewe Alex. | 1 - 0 | Darlington |
| 1948/1949 | F.A. Cup | 3rd Round | Sat 08 Jan | Rotherham U. | 4 - 2 | Darlington |
| 1947/1948 | F.A. Cup | 1st Round | Sat 29 Nov | Hartlepools | 1 - 0 | Darlington |
| 1946/1947 | F.A. Cup | 2nd Round | Sat 14 Dec | Darlington | 1 - 2 | Hull City |
| 1945/1946 | F.A. Cup | 2nd Round | Sat 15 Dec | Gateshead | 1 - 2 | Darlington |
| Gateshead won 5-4 on aggregate |
| 1938/1939 | F.A. Cup | 2nd Round | Sat 10 Dec | Chelmsford C. | 3 - 1 | Darlington |
| 1937/1938 | F.A. Cup | 1st Round | Sat 27 Nov | Darlington | 0 - 2 | Scarborough |
| 1936/1937 | F.A. Cup | 4th Round | Sat 30 Jan | West Brom. | 3 - 2 | Darlington |
| 1935/1936 | F.A. Cup | 3rd Round | Sat 11 Jan | Darlington | 2 - 3 | Bury |
| 1934/1935 | F.A. Cup | 2nd Round | Sat 08 Dec | Stockport Co. | 3 - 2 | Darlington |
| 1933/1934 | F.A. Cup | 1st Round | Sat 25 Nov | Chester | 6 - 1 | Darlington |
| 1932/1933 | F.A. Cup | 4th Round | Sat 28 Jan | Darlington | 0 - 2 | Chesterfield |
| 1931/1932 | F.A. Cup | 3rd Round Replay | Thu 14 Jan | Northampton | 2 - 0 | Darlington |
| 1930/1931 | F.A. Cup | 1st Round | Sat 29 Nov | Southport | 4 - 2 | Darlington |
| 1929/1930 | F.A. Cup | 1st Round | Sat 30 Nov | Caernarvon Ath | 4 - 2 | Darlington |
| 1928/1929 | F.A. Cup | 3rd Round | Sat 12 Jan | Darlington | 2 - 6 | Bury |
| 1927/1928 | F.A. Cup | 3rd Round | Sat 14 Jan | Liverpool | 1 - 0 | Darlington |
| 1926/1927 | F.A. Cup | 4th Round | Sat 29 Jan | Darlington | 0 - 2 | Cardiff City |
| 1925/1926 | F.A. Cup | 2nd Round | Sat 12 Dec | New Brighton | 2 - 0 | Darlington |
| 1924/1925 | F.A. Cup | 1st Round 2nd Replay | Mon 19 Jan | Cardiff City | 2 - 0 | Darlington |
| played at Anfield |
| 1923/1924 | F.A. Cup | 1st Round | Sat 12 Jan | Wolves | 3 - 1 | Darlington |
| 1921/1922 | F.A. Cup | 1st Round | Sat 07 Jan | Man. City | 3 - 1 | Darlington |
| 1920/1921 | F.A. Cup | 1st Round Replay | Wed 12 Jan | Blackpool | 2 - 1 | Darlington |
| 1919/1920 | F.A. Cup | 2nd Round | Sat 31 Jan | Birmingham | 4 - 0 | Darlington |
| 1914/1915 | F.A. Cup | 1st Round | Sat 09 Jan | Darlington | 0 - 1 | Bradford City |
| 1911/1912 | F.A. Cup | 2nd Round Replay | Thu 08 Feb | Northampton | 2 - 0 | Darlington |
| 1910/1911 | F.A. Cup | 3rd Round | Sat 25 Feb | Darlington | 0 - 3 | Swindon Town |
| 1887/1888 | F.A. Cup | 3rd Round | Sat 26 Nov | Darlington | 0 - 2 | Shankhouse |
| 1886/1887 | F.A. Cup | 1st Round | Sat 30 Oct | Horncastle | 2 - 0 | Darlington |
| 1885/1886 | F.A. Cup | 2nd Round | Sat 21 Nov | Grimsby Town | 8 - 0 | Darlington |
