| First Team Matches | Second Team Matches | Youth Matches | League Debuts | Associated with both clubs | Transfers | Ladies | Programmes |
| Seasons | Competition | Date | Venue | Results | Wolves Manager | Arsenal Manager | |
| As Royal Arsenal | |||||||
| 1891/92 | Friendly | 5 March 1892 | Invicta Ground | W | 4-1 | Jack Addenbrooke | Committee |
| 1892/93 | Friendly | 14 January 1893 | Invicta Ground | W | 3-1 | Jack Addenbrooke | Committee |
| As Woolwich Arsenal | |||||||
| 1893/94 | Friendly | 30 October 1893 | Manor Ground | L | 0-1 | Jack Addenbrooke | Committee |
| 1904/05 | Football League (1) | 24 September 1904 | Manor Ground | L | 0-2 | Jack Addenbrooke | Phil Kelso |
| 1904/05 | Football League (1) | 21 January 1905 | Molineux | W | 4-1 | Jack Addenbrooke | Phil Kelso |
| 1905/06 | Football League (1) | 7 October 1905 | Molineux | L | 0-2 | Jack Addenbrooke | Phil Kelso |
| 1905/06 | Football League (1) | 10 February 1906 | Manor Ground | L | 1-2 | Jack Addenbrooke | Phil Kelso |
| 1913/14 | Football League (2) | 13 September 1913 | Molineux | L | 1-2 | Jack Addenbrooke | George Morrell |
| 1913/14 | Football League (2) | 3 January 1914 | Highbury | L | 1-3 | Jack Addenbrooke | George Morrell |
| As Arsenal | |||||||
| 1914/15 | Football League (2) | 5 September 1914 | Molineux | W | 1-0 | Jack Addenbrooke | George Morrell |
| 1914/15 | Football League (2) | 2 January 1915 | Highbury | L | 1-5 | Jack Addenbrooke | George Morrell |
| 1925/26 | FA Cup | 9 January 1926 | Molineux | D | 1-1 | Albert Hoskins | Herbert Chapman |
| 1925/26 | FA Cup | 13 January 1926 | Highbury | L | 0-1 | Albert Hoskins | Herbert Chapman |
| 1926/27 | FA Cup | 5 March 1927 | Highbury | L | 1-2 | Fred Scotchbrook | Herbert Chapman |
| 1932/33 | Football League (1) | 5 November 1932 | Molineux | L | 1-7 | Major Frank Buckley | Herbert Chapman |
| 1932/33 | Football League (1) | 18 March 1933 | Highbury | W | 2-1 | Major Frank Buckley | Herbert Chapman |
| 1933/34 | Football League (1) | 11 November 1933 | Molineux | L | 0-1 | Major Frank Buckley | Herbert Chapman |
| 1933/34 | Football League (1) | 24 March 1934 | Highbury | L | 2-3 | Major Frank Buckley | Joe Shaw © |
| 1934/35 | Football League (1) | 1 December 1934 | Highbury | L | 0-7 | Major Frank Buckley | George Allison |
| 1934/35 | Football League (1) | 13 April 1935 | Molineux | D | 1-1 | Major Frank Buckley | George Allison |
| 1935/36 | Football League (1) | 23 November 1935 | Highbury | L | 0-4 | Major Frank Buckley | George Allison |
| 1935/36 | Football League (1) | 28 March 1936 | Molineux | D | 2-2 | Major Frank Buckley | George Allison |
| 1936/37 | Football League (1) | 19 September 1936 | Molineux | W | 2-0 | Major Frank Buckley | George Allison |
| 1936/37 | Football League (1) | 23 January 1937 | Highbury | L | 0-3 | Major Frank Buckley | George Allison |
| 1937/38 | Football League (1) | 4 September 1937 | Highbury | L | 0-5 | Major Frank Buckley | George Allison |
| 1937/38 | Football League (1) | 15 January 1938 | Molineux | W | 3-1 | Major Frank Buckley | George Allison |
| 1937/38 | FA Cup | 22 January 1938 | Molineux | L | 1-2 | Major Frank Buckley | George Allison |
| 1937/38 | Friendly | 24 April 1938 | Layer Road (Colchester) | W | 1-0 | Major Frank Buckley | George Allison |
| 1938/39 | Football League (1) | 17 September 1938 | Molineux | L | 0-1 | Major Frank Buckley | George Allison |
| 1938/39 | Football League (1) | 1 February 1939 | Highbury | D | 0-0 | Major Frank Buckley | George Allison |
| 1939/40 | Football League | 26 August 1939 | Molineux | D | 2-2* | Major Frank Buckley | George Allison |
| 1945/46 | War Competition | 3 September 1945 | Molineux | D | 1-1 | Ted Vizard | George Allison |
| 1945/46 | War Competition | 29 December 1945 | Highbury | L | 2-3 | Ted Vizard | George Allison |
| 1946/47 | Football League (1) | 31 August 1946 | Molineux | W | 6-1 | Ted Vizard | George Allison |
| 1946/47 | Football League (1) | 28 December 1946 | Highbury | D | 1-1 | Ted Vizard | George Allison |
| 1947/48 | Football League (1) | 18 October 1947 | Molineux | D | 1-1 | Ted Vizard | Tom Whittaker |
| 1947/48 | Football League (1) | 6 March 1948 | Highbury | L | 2-5 | Ted Vizard | Tom Whittaker |
| 1948/49 | Football League (1) | 25 September 1948 | Highbury | L | 1-3 | Stan Cullis | Tom Whittaker |
| 1948/49 | Football League (1) | 19 February 1949 | Molineux | L | 1-3 | Stan Cullis | Tom Whittaker |
| 1949/50 | Football League (1) | 3 December 1949 | Highbury | D | 1-1 | Stan Cullis | Tom Whittaker |
| 1949/50 | Football League (1) | 22 April 1950 | Molineux | W | 3-0 | Stan Cullis | Tom Whittaker |
| 1950/51 | Football League (1) | 4 November 1950 | Molineux | L | 0-1 | Stan Cullis | Tom Whittaker |
| 1950/51 | Football League (1) | 24 March 1951 | Highbury | L | 1-2 | Stan Cullis | Tom Whittaker |
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