| Chesterfield 1 v 0 Leyton Orient FA Cup Sunday, 3rd December 2023 Kick-off 14:00 |  |
Head to Head - Chesterfield v Leyton Orient
| HOME | AWAY | TOTAL | ||||||||||||||||
| Competition | P | W | D | L | F | A | W | D | L | F | A | W | D | L | F | A | ||
| Sky Bet Championship | 8 | 0 | 0 | 0 | 0 | 0 | 1 | 4 | 3 | 10 | 16 | 1 | 4 | 3 | 10 | 16 | ||
| Sky Bet League One | 8 | 0 | 0 | 0 | 0 | 0 | 4 | 3 | 1 | 9 | 7 | 4 | 3 | 1 | 9 | 7 | ||
| All League | 16 | 0 | 0 | 0 | 0 | 0 | 5 | 7 | 4 | 19 | 23 | 5 | 7 | 4 | 19 | 23 | ||
| FA Cup | 4 | 0 | 0 | 0 | 0 | 0 | 2 | 1 | 1 | 3 | 2 | 2 | 1 | 1 | 3 | 2 | ||
| Football League Div 3 | 2 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 2 | 1 | 6 | 0 | 0 | 2 | 1 | 6 | ||
| League Cup | 2 | 0 | 0 | 0 | 0 | 0 | 2 | 0 | 0 | 3 | 1 | 2 | 0 | 0 | 3 | 1 | ||
| Total: | 24 | 0 | 0 | 0 | 0 | 0 | 9 | 8 | 7 | 26 | 32 | 9 | 8 | 7 | 26 | 32 | ||
| Average goals scored: | 1.083 | ||||||||||||||||||||||||||||||||||||||||||||||
| Average goals conceded: | 1.333 | ||||||||||||||||||||||||||||||||||||||||||||||
| Win with greatest margin: | 1 |
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| Loss with greatest margin: | 4 |
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| Most goals in a match: | 6 |
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| 3 Dec 2023 | Emirates FA Cup | Chesterfield | 1-0 | Leyton Orient | L | |
| 14 Feb 2015 | Sky Bet League One | Chesterfield | 2-3 | Leyton Orient | W | |
| 9 Aug 2014 | Sky Bet League One | Leyton Orient | 1-2 | Chesterfield | W | |
| 14 Jan 2012 | EL3 | Leyton Orient | 1-1 | Chesterfield | D | |
| 3 Sep 2011 | EL3 | Chesterfield | 0-0 | Leyton Orient | D | |
| 10 Mar 2007 | EL3 | Chesterfield | 0-1 | Leyton Orient | W | |
| 7 Oct 2006 | EL3 | Leyton Orient | 0-0 | Chesterfield | D | |
| 16 Nov 2005 | FA Cup | Chesterfield | 1-2 | Leyton Orient | W | |
| 5 Nov 2005 | FA Cup | Leyton Orient | 0-0 | Chesterfield | D | |
| 7 Apr 2001 | Football League Div 3 | Leyton Orient | 2-0 | Chesterfield | L | |
| 2 Dec 2000 | Football League Div 3 | Chesterfield | 4-1 | Leyton Orient | L | |
| 15 Jan 1983 | EL3 | Leyton Orient | 2 - 0 | Chesterfield | L | |
| 28 Aug 1982 | EL3 | Chesterfield | 1 - 2 | Leyton Orient | W | |
| 30 Jan 1979 | League Cup | Leyton Orient | 1 - 2 | Chesterfield | W | |
| 14 Nov 1960 | League Cup | Leyton Orient | 0 - 1 | Chesterfield | W | |
| 9 Jan 1926 | FA Cup | Chesterfield | 0 - 1 | Leyton Orient | W | |
| 30 Jan 1909 | League Division Two | Leyton Orient | 1 - 1 | Chesterfield | D | |
| 26 Sep 1908 | League Division Two | Chesterfield | 2 - 0 | Leyton Orient | L | |
| 7 Mar 1908 | League Division Two | Chesterfield | 1 - 1 | Leyton Orient | D | |
| 9 Nov 1907 | League Division Two | Leyton Orient | 5 - 1 | Chesterfield | L | |
| 29 Mar 1907 | League Division Two | Chesterfield | 2 - 1 | Leyton Orient | L | |
| 26 Dec 1906 | League Division Two | Leyton Orient | 1 - 2 | Chesterfield | W | |
| 27 Jan 1906 | League Division Two | Chesterfield | 1 - 1 | Leyton Orient | D | |
| 23 Sep 1905 | League Division Two | Leyton Orient | 3 - 3 | Chesterfield | D |