| Date of match | Type of match | Name of team | Name of team | Score | Attendance |
| 1893-94 season | FA Cup 2nd qualifying round | Chesterfield Town | Derby Junction | 4-0 | - |
| 1894-95 season | FA Cup 1st qualifying round | Chesterfield Town | Clay Cross Town | 3-0 | - |
| 1894-95 season | FA Cup 3rd qualifying round | Chesterfield Town | Buxton | 4-0 | - |
| 1894-95 season | FA Cup 4th qualifying round replay | Chesterfield Town | Long Eaton Rangers | 3-0 | - |
| 1895-96 season | FA Cup 1st qualifying round | Chesterfield | Eckington Works | 1-0 | - |
| 1895-96 season | FA Cup 2nd qualifying round | Chesterfield | Long Eaton Rangers | 2-0 | - |
| 1895-96 season | FA Cup 3rd qualifying round | Chesterfield | Heanor Town | 3-0 | - |
| 1895-96 season | FA Cup 4th qualifying round | Chesterfield | Ilkeston Town | 2-0 | - |
| 1 February 1896 | FA Cup 1st round | Chesterfield | Newcastle United | 0-4 | 5,000 |
| 25 October 1933 | Division Three (North) Cup 1st round | Chesterfield | Doncaster Rovers | 3-2 | 2,703 |
| 14 February 1934 | Division Three (North) Cup 2nd round | Chesterfield | Rotherham United | 4-1 | 2,055 |
| 30 January 1935 | Division Three (North) Cup 1st round | Chesterfield | Mansfield Town | 8-1 | 1,501 |
| 13 February 1935 | Division Three (North) Cup 2nd round | Chesterfield | Rotherham United | 3-0 | 4,007 |
| 13 March 1935 | Division Three (North) Cup quarter-final | Chesterfield | Walsall | 1-1 | 2,000 |
| 20 November 1969 | FA Cup 1st round 2nd replay | Barrow | Alfreton Town | 2-2 | 7,369 |
| 31 July 1980 | Anglo-Scottish Cup English qualifiers Group 1 | Chesterfield | Sheffield United | 1-0 | 7,693 |
| 5 August 1980 | Anglo-Scottish Cup English qualifiers Group 1 | Chesterfield | Hull City | 1-1 | 4,945 |
| 28 October 1980 | Anglo-Scottish Cup quarter-final 2nd leg | Chesterfield | Rangers | 3-0 | 13,914 |
| 9 December 1980 | Anglo-Scottish Cup semi-final 2nd leg | Chesterfield | Bury | 1-1 | 6,400 |
| 24 March 1981 | Anglo-Scottish Cup final 1st leg | Chesterfield | Notts County | 1-0 | 10,190 |
| 21 August 1981 | Football League Group Cup Group C | Chesterfield | Sheffield United | 1-1 | 4,923 |
| 14 August 1982 | Football League Group Cup Group B | Chesterfield | Chester | 1-1 | 1,149 |
| 17 August 1982 | Football League Group Cup Group B | Chesterfield | Shrewsbury Town | 1-0 | 1,177 |
| 5 February 1985 | Freight Rover Trophy Northern section 1st round 2nd leg | Chesterfield | Rotherham United | 1-0 | 2,809 |
| 21 January 1986 | Freight Rover Trophy Northern section 1st round Group 2 | Chesterfield | Burnley | 1-2 | 1,053 |
| 2 December 1986 | Freight Rover Trophy Nothern section 1st round Group 1 | Chesterfield | Middlesbrough | 2-1 | 1,764 |
