| First Team Matches | Second Team Matches | Youth Team Matches | League debuts | Associated with both clubs | Transfers |
As Chesterfield Town
| Seasons | Competition | Date | Venue | Results | Wolves Manager | Chesterfield Manager | Referee | |
| 1906/07 | Football League (2) | 15 December 1906 | Molineux | W | 2-1 | Jack Addenbrooke | W Furness | J Pearson (Crewe) |
| 1906/07 | Football League (2) | 20 April 1907 | Recreation Ground | L | 2-3 | Jack Addenbrooke | George Swift | T Kirkham (Burslem) |
| 1907/08 | Football League (2) | 23 November 1907 | Molineux | D | 0-0 | Jack Addenbrooke | George Swift | T Kirkham (Burslem) |
| 1907/08 | Football League (2) | 21 March 1908 | Recreation Ground | L | 0-2 | Jack Addenbrooke | George Swift | T Kirkham (Burslem) |
| 1908/09 | Football League (2) | 12 September 1908 | Recreation Ground | D | 1-1 | Jack Addenbrooke | George Swift | J Pearson (Crewe) |
| 1908/09 | Football League (2) | 9 January 1909 | Molineux | W | 3-0 | Jack Addenbrooke | George Swift | J Pearson (Crewe) |
As Chesterfield
| 1923/24 | Football League (3N) | 25 August 1923 | Recreation Ground | D | 0-0 | George Jobey | Harry Parkes | H Griffiths (New Sawley, Derby) |
| 1923/24 | Football League (3N) | 1 September 1923 | Molineux | W | 2-1 | George Jobey | Harry Parkes | H Griffiths (New Sawley, Derby) |
| 1931/32 | Football League (2) | 12 September 1931 | Molineux | W | 6-0 | Major Frank Buckley | Ted Davison | W Bristow (Stafford) |
| 1931/32 | Football League (2) | 27 January 1932 | Recreation Ground | W | 2-1 | Major Frank Buckley | Ted Davison | W Barlow (Chesterfield) |
| 1948/49 | FA Cup | 8 January 1949 | Molineux | W | 6-0 | Stan Cullis | Bob Brocklebank | W Evans (Liverpool) |
| 1981/82 | Friendly | 10 August 1981 | Castlecroft | ab | John Barnwell | Frank Barlow | x | |
| 1985/86 | Football League (3) | 1 January 1986 | Molineux | W | 1-0 | Sammy Chapman | John Duncan | H Taylor (Oadby) |
| 1985/86 | Football League (3) | 29 March 1986 | Recreation Ground | L | 0-3 | Sammy Chapman | John Duncan | D Scott (Burnley) |
| 1988/89 | Football League (3) | 10 September 1988 | Recreation Ground | W | 3-0 | Graham Turner | Kevin Randall | J Worrall (Warrington) |
| 1988/89 | Football League (3) | 21 January 1989 | Molineux | W | 1-0 | Graham Turner | Paul Hart | J Deakin (Llantwit Major) |
| 1994/95 | FL Cup | 20 September 1994 | Recreation Ground | W | 3-1 | Graham Taylor | John Duncan | P Danson (Blaby) |
| 1994/95 | FL Cup | 27 September 1994 | Molineux | D | 1-1 | Graham Taylor | John Duncan | K Morton (Burton St Edmunds) |
| 2006/07 | FL Cup | 23 August 2006 | Recreation Ground | D | 0-0 | Mick McCarthy | Roy McFarland | P Joslin (Newark) |
| 2013/14 | Friendly | 23 July 2013 | Away | W | 2-1 | Kenny Jackett | Paul Cook | x |
