| 23.12.1899 | Chesterfield Town | 1 | - | 2 | L | 2.000 | LgDiv2 | U | Saltergate | William Griffiths | |||||
| 28.04.1900 | Chesterfield Town | 2 | - | 1 | W | 6.000 | LgDiv2 | H | Bank Street | Edward Holt, John Grundy | |||||
| 22.12.1900 | Chesterfield Town | 1 | - | 2 | L | 4.000 | LgDiv2 | U | Saltergate | Jim Hancock (o.g.) | |||||
| 27.04.1901 | Chesterfield Town | 1 | - | 0 | W | 1.000 | LgDiv2 | H | Bank Street | Thomas Leigh | |||||
| 17.03.1902 | Chesterfield Town | 0 | - | 3 | L | 2.000 | LgDiv2 | U | Saltergate | ||||||
| 23.04.1902 | Chesterfield Town | 2 | - | 0 | W | 2.000 | LgDiv2 | H | Bank Street | James Coupar, Stephen Preston | |||||
| 04.10.1902 | Chesterfield Town | 2 | - | 1 | W | 12.000 | LgDiv2 | H | Bank Street | Stephen Preston x2 | |||||
| 31.01.1903 | Chesterfield Town | 0 | - | 2 | L | 6.000 | LgDiv2 | U | Saltergate | ||||||
| 25.12.1903 | Chesterfield Town | 3 | - | 1 | W | 15.000 | LgDiv2 | H | Bank Street | Thomas Arkesden x2, Sandy Robertson | |||||
| 01.04.1904 | Chesterfield Town | 2 | - | 0 | W | 5.000 | LgDiv2 | U | Saltergate | Alexander Bell, Proctor Hall | |||||
| 26.12.1904 | Chesterfield Town | 3 | - | 0 | W | 20.000 | LgDiv2 | H | Bank Street | Jack Allan x2, Henry Williams | |||||
| 21.04.1905 | Chesterfield Town | 0 | - | 2 | L | 10.000 | LgDiv2 | U | Saltergate | ||||||
| 11.11.1905 | Chesterfield Town | 0 | - | 1 | L | 3.000 | LgDiv2 | U | Saltergate | ||||||
| 17.03.1906 | Chesterfield Town | 4 | - | 1 | W | 16.000 | LgDiv2 | H | Bank Street | Jack Picken x3, Chalres Sagar | |||||
| 26.09.1931 | Chesterfield | 3 | - | 1 | W | 10.834 | LgDiv2 | H | Old Trafford | William Johnston, Arthur Warburton x2 | |||||
| 06.02.1932 | Chesterfield | 3 | - | 1 | W | 9.457 | LgDiv2 | U | Saltergate | Thomas Reid x2, Joe Spence | |||||
| 26.11.1932 | Chesterfield | 1 | - | 1 | D | 10.277 | LgDiv2 | U | Saltergate | William Ridding | |||||
| 08.04.1933 | Chesterfield | 2 | - | 1 | W | 16.031 | LgDiv2 | H | Old Trafford | Neil Dewar, Thomas Frame | |||||
| 13.11.1937 | Chesterfield | 7 | - | 1 | W | 17.407 | LgDiv2 | U | Saltergate | Thomas Bamford x4, William Bryant, Thomas Manley, Harry Baird | |||||
| 26.03.1938 | Chesterfield | 4 | - | 1 | W | 27.311 | LgDiv2 | H | Old Trafford | William Bryant, Johnny Carey, Jack Smith x2 |