| Chesterfield 3 v 0 Southend United Saturday, 27th January 2024 Kick-off 15:00 |  |
Head to Head - Chesterfield v Southend United
| HOME | AWAY | TOTAL | ||||||||||||||||
| Competition | P | W | D | L | F | A | W | D | L | F | A | W | D | L | F | A | ||
| Sky Bet League One | 32 | 0 | 0 | 0 | 0 | 0 | 12 | 6 | 14 | 44 | 49 | 12 | 6 | 14 | 44 | 49 | ||
| EL4 | 20 | 0 | 0 | 0 | 0 | 0 | 5 | 5 | 10 | 19 | 31 | 5 | 5 | 10 | 19 | 31 | ||
| All League | 52 | 0 | 0 | 0 | 0 | 0 | 17 | 11 | 24 | 63 | 80 | 17 | 11 | 24 | 63 | 80 | ||
| EL5 | 2 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 2 | 1 | 5 | 0 | 0 | 2 | 1 | 5 | ||
| FA Cup | 7 | 0 | 0 | 0 | 0 | 0 | 2 | 2 | 3 | 11 | 13 | 2 | 2 | 3 | 11 | 13 | ||
| Football League Div 3 | 2 | 0 | 0 | 0 | 0 | 0 | 0 | 1 | 1 | 3 | 4 | 0 | 1 | 1 | 3 | 4 | ||
| Total: | 63 | 0 | 0 | 0 | 0 | 0 | 19 | 14 | 30 | 78 | 102 | 19 | 14 | 30 | 78 | 102 | ||
| Average goals scored: | 1.238 | ||||||||||||||||
| Average goals conceded: | 1.619 | ||||||||||||||||
| Win with greatest margin: | 4 |
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| Loss with greatest margin: | 4 |
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| Most goals in a match: | 7 |
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| 27 Jan 2024 | EL5 | Chesterfield | 3-0 | Southend United | L | |
| 18 Nov 2023 | EL5 | Southend United | 2-1 | Chesterfield | L | |
| 6 Nov 2021 | Emirates FA Cup | Chesterfield | 3-1 | Southend United | L | |
| 14 Apr 2017 | Sky Bet League One | Chesterfield | 0-4 | Southend United | W | |
| 15 Oct 2016 | Sky Bet League One | Southend United | 1-0 | Chesterfield | L | |
| 5 Mar 2016 | Sky Bet League One | Southend United | 0-1 | Chesterfield | W | |
| 20 Oct 2015 | Sky Bet League One | Chesterfield | 3-0 | Southend United | L | |
| 18 Jan 2014 | EL4 | Southend United | 3-0 | Chesterfield | L | |
| 7 Dec 2013 | Budweiser FA Cup | Chesterfield | 1-3 | Southend United | W | |
| 24 Aug 2013 | EL4 | Chesterfield | 2-1 | Southend United | L | |
| 26 Jan 2013 | EL4 | Chesterfield | 0-1 | Southend United | W | |
| 21 Dec 2012 | EL4 | Southend United | 3-0 | Chesterfield | L | |
| 8 Jan 2011 | EL4 | Southend United | 2-3 | Chesterfield | W | |
| 9 Oct 2010 | EL4 | Chesterfield | 2-1 | Southend United | L | |
| 18 Feb 2006 | EL3 | Chesterfield | 3-4 | Southend United | W | |
| 6 Dec 2005 | EL3 | Southend United | 0-0 | Chesterfield | D | |
| 18 Dec 2001 | AXA FA Cup | Southend United | 2-0 | Chesterfield | L | |
| 8 Dec 2001 | AXA FA Cup | Chesterfield | 1-1 | Southend United | D | |
| 31 Mar 2001 | Football League Div 3 | Chesterfield | 1-1 | Southend United | D | |
| 16 Dec 2000 | Football League Div 3 | Southend United | 3-2 | Chesterfield | L | |
| 3 Apr 1998 | EL4 | Southend United | 0 - 2 | Chesterfield | W | |
| 29 Nov 1997 | EL4 | Chesterfield | 1 - 0 | Southend United | L | |
| 7 Apr 1990 | EL4 | Southend United | 0 - 2 | Chesterfield | W | |
| 28 Oct 1989 | EL4 | Chesterfield | 1 - 1 | Southend United | D | |
| 4 Mar 1989 | EL3 | Chesterfield | 2 - 1 | Southend United | L | |
| 22 Oct 1988 | EL3 | Southend United | 3 - 1 | Chesterfield | L | |
| 25 Mar 1988 | EL3 | Southend United | 3 - 0 | Chesterfield | L | |
| 24 Oct 1987 | EL3 | Chesterfield | 3 - 1 | Southend United | L | |
| 23 Apr 1985 | EL4 | Southend United | 0 - 1 | Chesterfield | W | |
| 8 Sep 1984 | EL4 | Chesterfield | 2 - 1 | Southend United | L | |
| 15 Mar 1983 | EL3 | Chesterfield | 0 - 2 | Southend United | W | |
| 6 Sep 1982 | EL3 | Southend United | 2 - 0 | Chesterfield | L | |
| 5 Mar 1982 | EL3 | Southend United | 0 - 2 | Chesterfield | W | |
| 17 Oct 1981 | EL3 | Chesterfield | 1 - 2 | Southend United | W | |
| 8 Mar 1980 | EL3 | Chesterfield | 1 - 0 | Southend United | L | |
| 26 Oct 1979 | EL3 | Southend United | 0 - 0 | Chesterfield | D | |
| 2 Feb 1979 | EL3 | Southend United | 2 - 0 | Chesterfield | L | |
| 27 Sep 1978 | EL3 | Chesterfield | 3 - 2 | Southend United | L | |
| 19 Apr 1976 | EL3 | Southend United | 1 - 1 | Chesterfield | D | |
| 27 Dec 1975 | EL3 | Chesterfield | 1 - 2 | Southend United | W | |
| 19 Mar 1975 | EL3 | Chesterfield | 1 - 1 | Southend United | D | |
| 17 Aug 1974 | EL3 | Southend United | 2 - 1 | Chesterfield | L | |
| 5 Apr 1974 | EL3 | Southend United | 1 - 3 | Chesterfield | W | |
| 14 Nov 1973 | EL3 | Chesterfield | 0 - 0 | Southend United | D | |
| 21 Apr 1973 | EL3 | Southend United | 5 - 1 | Chesterfield | L | |
| 7 Mar 1973 | EL3 | Chesterfield | 2 - 4 | Southend United | W | |
| 31 Mar 1970 | EL4 | Chesterfield | 3 - 0 | Southend United | L | |
| 1 Nov 1969 | EL4 | Southend United | 0 - 0 | Chesterfield | D | |
| 25 Apr 1969 | EL4 | Chesterfield | 0 - 0 | Southend United | D | |
| 3 Mar 1969 | EL4 | Southend United | 2 - 2 | Chesterfield | D | |
| 13 Apr 1968 | EL4 | Southend United | 1 - 1 | Chesterfield | D | |
| 7 Oct 1967 | EL4 | Chesterfield | 3 - 1 | Southend United | L | |
| 15 Apr 1967 | EL4 | Southend United | 4 - 1 | Chesterfield | L | |
| 19 Nov 1966 | EL4 | Chesterfield | 2 - 1 | Southend United | L | |
| 31 Dec 1960 | EL3 | Southend United | 1 - 1 | Chesterfield | D | |
| 27 Aug 1960 | EL3 | Chesterfield | 0 - 3 | Southend United | W | |
| 9 Apr 1960 | EL3 | Chesterfield | 1 - 0 | Southend United | L | |
| 21 Nov 1959 | EL3 | Southend United | 1 - 2 | Chesterfield | W | |
| 17 Jan 1959 | EL3 | Southend United | 2 - 5 | Chesterfield | W | |
| 6 Sep 1958 | EL3 | Chesterfield | 4 - 0 | Southend United | L | |
| 12 Dec 1953 | FA Cup | Southend United | 1 - 2 | Chesterfield | W | |
| 16 Jan 1939 | FA Cup | Southend United | 4 - 3 | Chesterfield | L | |
| 11 Jan 1939 | FA Cup | Chesterfield | 1 - 1 | Southend United | D |