| L1 | 2016-2017 | 01/04/2017 | Bolton Wanderers | 0-0 | Chesterfield | | Highlights | 23,376 | Draw |
| L1 | 2016-2017 | 17/12/2016 | Chesterfield | 1-0 | Bolton Wanderers | | Highlights | 6,924 | Loss |
| FAC4 | 1996-1997 | 04/02/1997 | Bolton Wanderers | 2-3 | Chesterfield | Taylor S, Green | | 10,852 | Loss |
| FAC2 | 1990-1991 | 11/12/1990 | Chesterfield | 3-4 | Bolton Wanderers | Reeves, Philliskirk, Thompson S, Storer | | 4,836 | Win |
| D3 | 1988-1989 | 14/03/1989 | Chesterfield | 1-1 | Bolton Wanderers | Thompson S | | 2,877 | Draw |
| FAC1R | 1988-1989 | 28/11/1988 | Chesterfield | 2-3 | Bolton Wanderers | Stevens I, Storer, Darby | | 4,168 | Win |
| FAC1 | 1988-1989 | 19/11/1988 | Bolton Wanderers | 0-0 | Chesterfield | | | 4,840 | Draw |
| D3 | 1988-1989 | 29/10/1988 | Bolton Wanderers | 5-0 | Chesterfield | Brown P 2, Morgan T 2, Stevens I | | 4,783 | Win |
| D3 | 1986-1987 | 28/02/1987 | Chesterfield | 0-0 | Bolton Wanderers | | | 3,202 | Draw |
| D3 | 1986-1987 | 30/09/1986 | Bolton Wanderers | 1-2 | Chesterfield | Caldwell | | 3,931 | Loss |
| D3 | 1985-1986 | 03/05/1986 | Chesterfield | 3-0 | Bolton Wanderers | | | 3,183 | Loss |
| D3 | 1985-1986 | 14/12/1985 | Bolton Wanderers | 2-1 | Chesterfield | Thompson S, Hartford | | 3,621 | Win |
| D3 | 1972-1973 | 04/11/1972 | Chesterfield | 0-1 | Bolton Wanderers | Lee S | | 6,576 | Win |
| D3 | 1972-1973 | 27/09/1972 | Bolton Wanderers | 1-0 | Chesterfield | Waldron | | 6,532 | Win |
| D3 | 1971-1972 | 04/03/1972 | Bolton Wanderers | 1-0 | Chesterfield | Wright R | | 5,607 | Win |
| D3 | 1971-1972 | 13/11/1971 | Chesterfield | 2-1 | Bolton Wanderers | Hunt R | | 9,423 | Loss |
| FAC1 | 1910-1911 | 14/01/1911 | Bolton Wanderers | 0-2 | Chesterfield | | | 6,193 | Loss |
| D2 | 1908-1909 | 20/02/1909 | Bolton Wanderers | 4-0 | Chesterfield | Hunter, Barber, Owen J, Hughes W | | Unknown | Win |
| D2 | 1908-1909 | 14/11/1908 | Chesterfield | 0-2 | Bolton Wanderers | Hogan 2 | | Unknown | Win |
| D2 | 1904-1905 | 11/02/1905 | Bolton Wanderers | 4-3 | Chesterfield | Marsh S 2 (1 pen), Wilson T, Shepherd | | Unknown | Win |
| D2 | 1904-1905 | 15/10/1904 | Chesterfield | 1-0 | Bolton Wanderers | | | Unknown | Loss |
| D2 | 1903-1904 | 13/04/1904 | Chesterfield | 1-1 | Bolton Wanderers | Taylor R | | Unknown | Draw |
| D2 | 1903-1904 | 26/12/1903 | Bolton Wanderers | 4-0 | Chesterfield | Greenhalgh S, Stokes, Taylor R, Boyd | | Unknown | Win |
| D2 | 1899-1900 | 14/04/1900 | Bolton Wanderers | 3-0 | Chesterfield | Picken J, Gilligan A, Morgan H | | Unknown | Win |
| D2 | 1899-1900 | 06/12/1899 | Chesterfield | 3-3 | Bolton Wanderers | Jack R, Barlow, Picken J | | Unknown | Draw |