| First Team Matches | Youth Team Matches | League Debuts | Associated with both clubs | Transfers |
| Season | Competition | Date | Venue | wld | Results | |
| 1906/07 | Football League | 22 December 1906 | Millfields | L | 0-4 | As Clapton Orient |
| 1906/07 | Football League | 27 December 1906 | Molineux | W | 6-1 | |
| 1907/08 | Football League | 14 December 1907 | Millfields | D | 1-1 | |
| 1907/08 | Football League | 11 April 1908 | Molineux | W | 2-0 | |
| 1908/09 | Football League | 5 December 1908 | Molineux | W | 5-1 | |
| 1908/09 | Football League | 10 April 1909 | Millfields | W | 3-1 | |
| 1909/10 | Football League | 13 September 1909 | Molineux | W | 3-1 | |
| 1910/11 | Football League | 1 October 1910 | Molineux | W | 1-0 | |
| 1909/10 | Football League | 25 October 1910 | Millfields | L | 0-1 | |
| 1910/11 | Football League | 20 March 1911 | Millfields | L | 1-3 | |
| 1911/12 | Football League | 23 September 1911 | Molineux | L | 0-1 | |
| 1911/12 | Football League | 27 January 1912 | Millfields | L | 0-1 | |
| 1912/13 | Football League | 21 December 1912 | Molineux | D | 1-1 | |
| 1912/13 | Football League | 21 March 1913 | Millfields | D | 0-0 | |
| 1913/14 | Football League | 18 October 1913 | Millfields | D | 2-2 | |
| 1913/14 | Football League | 21 February 1914 | Molineux | W | 2-0 | |
| 1914/15 | Football League | 1 September 1914 | Millfields | D | 1-1 | |
| 1914/15 | Football League | 7 September 1914 | Molineux | D | 0-0 | |
| 1919/20 | Football League | 13 September 1919 | Millfields | D | 0-0 | |
| 1919/20 | Football League | 20 September 1919 | Molineux | L | 1-2 | |
| 1921/22 | Football League | 18 March 1921 | Molineux | L | 0-2 | |
| 1920/21 | Football League | 25 March 1921 | Millfields | W | 1-0 | |
| 1921/22 | Football League | 25 March 1921 | Millfields | L | 0-1 | |
| 1920/21 | Football League | 28 March 1921 | Molineux | L | 0-2 | |
| 1922/23 | Football League | 20 January 1923 | Molineux | L | 1-3 | |
| 1922/23 | Football League | 27 January 1923 | Millfields | L | 1-4 | |
| 1924/25 | Football League | 5 December 1924 | Molineux | L | 1-2 | |
| 1924/25 | Friendly | 31 January 1925 | Millfields | D | 1-1 | |
| 1924/25 | Football League | 11 April 1925 | Millfields | L | 1-2 | |
| 1925/26 | Football League | 21 November 1925 | Millfields | L | 1-2 | |
| 1925/26 | Football League | 3 April 1926 | Molineux | W | 3-0 | |
| 1926/27 | Football League | 18 September 1926 | Millfields | L | 0-2 | |
| 1926/27 | Football League | 5 February 1927 | Molineux | W | 5-0 | |
| 1927/28 | Football League | 24 December 1927 | Molineux | W | 5-3 | |
| 1927/28 | Football League | 5 May 1928 | Millfields | D | 0-0 | |
| 1928/29 | Football League | 15 December 1928 | Molineux | W | 3-2 | |
| 1928/29 | Football League | 27 April 1929 | Millfields | L | 0-2 | |
| 1962/63 | Football League | 24 November 1962 | Brisbane Road | W | 4-0 | As Leyton Orient |
| 1962/63 | Football League | 30 March 1963 | Molineux | W | 2-1 | |
| 1965/66 | Football League | 9 October 1965 | Brisbane Road | W | 3-0 | |
| 1965/66 | Football League | 1 January 1966 | Molineux | W | 2-1 | |
| 1972/73 | FL Cup | 5 September 1972 | Molineux | W | 2-1 | As Orient |
| 1976/77 | Football League | 27 November 1976 | Brisbane Road | W | 4-2 | |
| 1976/77 | Football League | 23 April 1977 | Molineux | W | 1-0 | |
| 1986/87 | Football League | 25 October 1986 | Molineux | W | 3-1 | |
| 1986/87 | Football League | 7 March 1987 | Brisbane Road | L | 1-3 | |
| 1987/88 | Football League | 19 December 1987 | Molineux | W | 2-0 | As Leyton Orient |
| 1987/88 | Football League | 7 May 1988 | Brisbane Road | W | 2-0 | |
| 2013/14 | Football League | 29 December 2013 | Molineux Stadium | D | 1-1 | |
| 2013/14 | Football League | 21 April 2014 | Brisbane Road | W | 3-1 |
