Chesterfield have played Darlington 84 times in competitive football, winning 33, drawing 24 and losing 27, first meeting on 10 Sep 1921 and most recently on 20 Feb 2010. Every meeting is listed below.
| Date | Season | Competition | Venue | Opponent | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 10 Sep 1921 | 1921–22 | Third Division North | A | Darlington | 0–7 | ||
| 17 Sep 1921 | 1921–22 | Third Division North | H | Darlington | 0–3 | ||
| 14 Apr 1923 | 1922–23 | Third Division North | A | Darlington | 1–4 | Sharp 59 | |
| 21 Apr 1923 | 1922–23 | Third Division North | H | Darlington | 0–0 | ||
| 29 Dec 1923 | 1923–24 | Third Division North | A | Darlington | 1–2 | Crockford 82 | |
| 5 Jan 1924 | 1923–24 | Third Division North | H | Darlington | 5–1 | Crockford 19, Crockford 51, Crockford 80, Birch 25, Whitfield 26 | |
| 18 Oct 1924 | 1924–25 | Third Division North | H | Darlington | 0–1 | ||
| 21 Feb 1925 | 1924–25 | Third Division North | A | Darlington | 3–3 | Whitfield 20, Fisher 38, Fisher 70 | |
| 22 Oct 1927 | 1927–28 | Third Division North | H | Darlington | 1–3 | Clayson 40 | |
| 26 Nov 1927 | 1927–28 | FA Cup | A | Darlington | 1–4 | Roseboom 47 | |
| 3 Mar 1928 | 1927–28 | Third Division North | A | Darlington | 2–4 | Oxley 65, Nutter 78 | |
| 13 Oct 1928 | 1928–29 | Third Division North | A | Darlington | 2–2 | Roseboom 30, Castle 67 | |
| 23 Feb 1929 | 1928–29 | Third Division North | H | Darlington | 2–1 | Castle 79, Sam Taylor 82 | |
| 14 Sep 1929 | 1929–30 | Third Division North | H | Darlington | 4–1 | Bullock 42, Bullock 43, Bullock 47, S Taylor 70 | |
| 18 Jan 1930 | 1929–30 | Third Division North | A | Darlington | 4–1 | Bullock 47, Bullock 68, Bullock 78, S Taylor 88 | |
| 22 Nov 1930 | 1930–31 | Third Division North | A | Darlington | 1–5 | Pynegar 37 | |
| 28 Mar 1931 | 1930–31 | Third Division North | H | Darlington | 2–1 | Pynegar 23, Abel 56 | |
| 28 Jan 1933 | 1932–33 | FA Cup | A | Darlington | 2–0 | Austin 7, Lee 77 | |
| 25 Dec 1933 | 1933–34 | Third Division North | H | Darlington | 0–1 | ||
| 26 Dec 1933 | 1933–34 | Third Division North | A | Darlington | 1–1 | Cook 7 | |
| 1 Dec 1934 | 1934–35 | Third Division North | H | Darlington | 2–2 | Sliman 60, Callender 85 | |
| 13 Apr 1935 | 1934–35 | Third Division North | A | Darlington | 1–2 | AR Brown 30 | |
| 2 Nov 1935 | 1935–36 | Third Division North | H | Darlington | 5–1 | Clifton 46, Dando 68, Dando 70, Dando 85, Spence 80 | |
| 7 Mar 1936 | 1935–36 | Third Division North | A | Darlington | 2–1 | Dando 6, Dando 26 | |
| 17 Nov 1951 | 1951–52 | Third Division North | H | Darlington | 4–2 | ||
| 5 Apr 1952 | 1951–52 | Third Division North | A | Darlington | 0–3 | ||
| 24 Sep 1952 | 1952–53 | Third Division North | A | Darlington | 1–3 | Southall | |
| 11 Apr 1953 | 1952–53 | Third Division North | H | Darlington | 3–0 | Harvey 29, Harvey 48, Westcott 70 | |
| 19 Aug 1953 | 1953–54 | Third Division North | H | Darlington | 1–1 | GB Smith | |
| 31 Mar 1954 | 1953–54 | Third Division North | A | Darlington | 2–3 | ||
| 28 Aug 1954 | 1954–55 | Third Division North | H | Darlington | 2–0 | George Smith, Watson | |
| 1 Jan 1955 | 1954–55 | Third Division North | A | Darlington | 2–0 | Marsden 18, Marsden 44 | |
| 24 Aug 1955 | 1955–56 | Third Division North | H | Darlington | 2–1 | Sowden 36, George Smith 61 | |
| 31 Aug 1955 | 1955–56 | Third Division North | A | Darlington | 1–2 | Sowden 35 | |
| 30 Mar 1957 | 1956–57 | Third Division North | A | Darlington | 1–4 | Cunliffe 57 | |
| 1 May 1957 | 1956–57 | Third Division North | H | Darlington | 4–1 | Frear 7, Whitehurst 17, Lewis 65, George Smith | |
| 14 Dec 1957 | 1957–58 | Third Division North | A | Darlington | 0–2 | ||
| 26 Apr 1958 | 1957–58 | Third Division North | H | Darlington | 2–0 | Frear 29, Dave Blakey 51 | |
| 18 Nov 1961 | 1961–62 | Fourth Division | H | Darlington | 1–1 | Lovie 3 | |
| 7 Apr 1962 | 1961–62 | Fourth Division | A | Darlington | 4–4 | ||
| 5 Sep 1962 | 1962–63 | League Cup | A | Darlington | 0–1 | ||
| 20 Oct 1962 | 1962–63 | Fourth Division | A | Darlington | 1–2 | Dave Blakey 4 | |
| 9 Mar 1963 | 1962–63 | Fourth Division | H | Darlington | 6–1 | Lovie 5, Poole 20, Duncan 26, Meredith 43, Clarke 54, Rackstraw 65 | |
| 30 Nov 1963 | 1963–64 | Fourth Division | A | Darlington | 2–3 | ||
| 11 Apr 1964 | 1963–64 | Fourth Division | H | Darlington | 2–1 | Gerry Sears 42, Rackstraw 70 | |
| 19 Oct 1964 | 1964–65 | Fourth Division | A | Darlington | 2–2 | McCann, Stringfellow | |
| 29 Mar 1965 | 1964–65 | Fourth Division | H | Darlington | 3–0 | ||
| 20 Nov 1965 | 1965–66 | Fourth Division | H | Darlington | 1–2 | Hollett 47 | |
| 16 Apr 1966 | 1965–66 | Fourth Division | A | Darlington | 1–4 | Hollett 37 | |
| 30 Sep 1967 | 1967–68 | Fourth Division | H | Darlington | 3–1 | Hollett 14, Hollett 43, Lord 20 | |
| 10 Feb 1968 | 1967–68 | Fourth Division | A | Darlington | 1–1 | Moore 22 | |
| 2 Nov 1968 | 1968–69 | Fourth Division | H | Darlington | 2–2 | ||
| 11 Jan 1969 | 1968–69 | Fourth Division | A | Darlington | 3–1 | ||
| 23 Aug 1969 | 1969–70 | Fourth Division | A | Darlington | 1–0 | Tom Fenoughty 77 | |
| 26 Dec 1969 | 1969–70 | Fourth Division | H | Darlington | 2–0 | John Archer 4, Kevin Randall 60 | |
| 25 Nov 1978 | 1978–79 | FA Cup | A | Darlington | 1–1 | Flavell 23 | |
| 6 Dec 1978 | 1978–79 | FA Cup | H | Darlington | 0–1 | ||
| 9 Aug 1980 | 1980–81 | League Cup | H | Darlington | 1–0 | Walker 45 | |
| 12 Aug 1980 | 1980–81 | League Cup | A | Darlington | 2–1 | Wilson 64, Ernie Moss 75 | |
| 29 Oct 1983 | 1983–84 | Fourth Division | H | Darlington | 1–1 | Bell 71 | |
| 18 Feb 1984 | 1983–84 | Fourth Division | A | Darlington | 1–2 | Waddington 19 | |
| 6 Oct 1984 | 1984–85 | Fourth Division | H | Darlington | 0–0 | ||
| 23 Mar 1985 | 1984–85 | Fourth Division | A | Darlington | 3–1 | Newton 62, Newton 88, Kendal 64 | |
| 17 Sep 1985 | 1985–86 | Third Division | H | Darlington | 1–0 | Ernie Moss 55 | |
| 22 Apr 1986 | 1985–86 | Third Division | A | Darlington | 1–2 | Bellamy 28 | |
| 27 Dec 1986 | 1986–87 | Third Division | A | Darlington | 1–1 | Jamie Hewitt 57 | |
| 4 May 1987 | 1986–87 | Third Division | H | Darlington | 1–0 | Coyle 2 | |
| 22 Dec 1990 | 1990–91 | Fourth Division | A | Darlington | 0–1 | ||
| 1 Apr 1991 | 1990–91 | Fourth Division | H | Darlington | 2–2 | ||
| 16 Nov 1991 | 1991–92 | FA Cup | A | Darlington | 1–2 | Cooke 12 | |
| 1 Sep 1992 | 1992–93 | Third Division | H | Darlington | 2–0 | Norris 45, Norris 80 | |
| 20 Feb 1993 | 1992–93 | Third Division | A | Darlington | 1–1 | Andy Morris 77 | |
| 4 Sep 1993 | 1993–94 | Third Division | H | Darlington | 1–1 | Norris 90 | |
| 8 Mar 1994 | 1993–94 | Third Division | A | Darlington | 0–0 | ||
| 15 Oct 1994 | 1994–95 | Third Division | H | Darlington | 0–0 | ||
| 29 Apr 1995 | 1994–95 | Third Division | A | Darlington | 1–0 | Lormor 35 | |
| 26 Dec 2000 | 2000–01 | Third Division | H | Darlington | 2–0 | ||
| 20 Jan 2001 | 2000–01 | Third Division | A | Darlington | 3–0 | ||
| 27 Oct 2007 | 2007–08 | League Two | A | Darlington | 0–0 | 4,205 | |
| 19 Apr 2008 | 2007–08 | League Two | H | Darlington | 1–1 | Jamie Ward 50 | 3,809 |
| 28 Dec 2008 | 2008–09 | League Two | A | Darlington | 0–0 | 3,352 | |
| 11 Apr 2009 | 2008–09 | League Two | H | Darlington | 0–0 | 3,642 | |
| 21 Nov 2009 | 2009–10 | League Two | H | Darlington | 5–2 | ||
| 20 Feb 2010 | 2009–10 | League Two | A | Darlington | 3–2 |
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