| First Team Matches | Youth Team Matches | League Debuts | Associated with both clubs | Transfers |
As Clapton Orient
| Seasons | Competition | Date | Venue | Results | Wolves Manager | Orient Manager | Referee | |
| 1906/07 | Football League (2) | 22 December 1906 | Millfields Road | L | 0-4 | Jack Addenbrooke | Billy Holmes | J Bailey (Leicester) |
| 1906/07 | Football League (2) | 27 December 1906 | Molineux | W | 6-1 | Jack Addenbrooke | Billy Holmes | J Bailey (Leicester) |
| 1907/08 | Football League (2) | 14 December 1907 | Millfields Road | D | 1-1 | Jack Addenbrooke | Billy Holmes | Lieut W Clover (Leicester) |
| 1907/08 | Football League (2) | 11 April 1908 | Molineux | W | 2-0 | Jack Addenbrooke | Billy Holmes | R Eccles (Darwen) |
| 1908/09 | Football League (2) | 5 December 1908 | Molineux | W | 5-1 | Jack Addenbrooke | Billy Holmes | J Bailey (Leicester) |
| 1908/09 | Football League (2) | 10 April 1909 | Millfields Road | W | 3-1 | Jack Addenbrooke | Billy Holmes | J Sharpe (Lichfield) |
| 1909/10 | Football League (2) | 13 September 1909 | Molineux | W | 3-1 | Jack Addenbrooke | Billy Holmes | J Sharpe (Lichfield) |
| 1909/10 | Football League (2) | 25 October 1909 | Millfields Road | L | 0-1 | Jack Addenbrooke | Billy Holmes | J Sharpe (Lichfield) |
| 1910/11 | Football League (2) | 1 October 1910 | Molineux | W | 1-0 | Jack Addenbrooke | Billy Holmes | H Dale (Manchester) |
| 1910/11 | Football League (2) | 20 March 1911 | Millfields Road | L | 1-3 | Jack Addenbrooke | Billy Holmes | H Dale (Manchester) |
| 1911/12 | Football League (2) | 23 September 1911 | Molineux | L | 0-1 | Jack Addenbrooke | Billy Holmes | J Bailey (Leicester) |
| 1911/12 | Football League (2) | 27 January 1912 | Millfields Road | L | 0-1 | Jack Addenbrooke | Billy Holmes | J Bailey (Leicester) |
| 1912/13 | Football League (2) | 26 December 1912 | Molineux | D | 1-1 | Jack Addenbrooke | Billy Holmes | P Sant (Barnsley) |
| 1912/13 | Football League (2) | 21 March 1913 | Millfields Road | D | 0-0 | Jack Addenbrooke | Billy Holmes | P Sant (Barnsley) |
| 1913/14 | Football League (2) | 18 October 1913 | Millfields Road | D | 2-2 | Jack Addenbrooke | Billy Holmes | G Pardoe (Kidderminster) |
| 1913/14 | Football League (2) | 21 February 1914 | Molineux | W | 2-1 | Jack Addenbrooke | Billy Holmes | G Pardoe (Kidderminster) |
| 1913/14 | Football League (2) | 1 September 1914 | Millfields Road | D | 1-1 | Jack Addenbrooke | Billy Holmes | A Pellowe (Oldham) |
| 1914/15 | Football League (2) | 7 September 1914 | Molineux | D | 0-0 | Jack Addenbrooke | Billy Holmes | A Pellowe (Oldham) |
| 1919/20 | Football League (2) | 13 September 1919 | Millfields Road | D | 0-0 | Jack Addenbrooke | Billy Holmes | T Prescott (Lincoln) |
| 1919/20 | Football League (2) | 20 September 1919 | Molineux | L | 1-2 | Jack Addenbrooke | Billy Holmes | T Prescott (Lincoln) |
| 1920/21 | Football League (2) | 25 March 1921 | Millfields Road | W | 1-0 | Jack Addenbrooke | Billy Holmes | E Pullan (Leeds) |
| 1920/21 | Football League (2) | 28 March 1921 | Molineux | L | 0-2 | Jack Addenbrooke | Billy Holmes | E Pullan (Leeds) |
| 1921/22 | Football League (2) | 18 March 1922 | Molineux | L | 0-2 | Jack Addenbrooke | Committee | W Russell (Swindon) |
| 1921/22 | Football League (2) | 25 March 1922 | Millfields Road | L | 0-1 | Jack Addenbrooke | Committee* | W Russell (Swindon) |
| 1922/23 | Football League (2) | 20 January 1923 | Molineux | L | 1-3 | George Jobey | Peter Proudfoot | H Mason (Erdington, B’ham) |
| 1922/23 | Football League (2) | 27 January 1923 | Millfields Road | L | 1-4 | George Jobey | Peter Proudfoot | H Mason (Erdington, B’ham) |
| 1924/25 | Football League (2) | 6 December 1924 | Molineux | L | 1-2 | Albert Hoskins | Peter Proudfoot | E Pinckston (Handsworth) |
| 1924/25 | Friendly | 31 January 1925 | Millfields Road | D | 1-1 | Albert Hoskins | Peter Proudfoot | x |
| 1924/25 | Football League (2) | 11 April 1925 | Millfields Road | L | 1-2 | Albert Hoskins | Peter Proudfoot | E Pinckston (Handsworth) |
| 1925/26 | Football League (2) | 21 November 1925 | Millfields Road | L | 1-2 | Albert Hoskins | Peter Proudfoot | G Watson (West Bridgford) |
| 1925/26 | Football League (2) | 3 April 1926 | Molineux | W | 3-0 | Fred Scotchbrook | Peter Proudfoot | G Watson (West Bridgford) |
| 1926/27 | Football League (2) | 18 September 1926 | Millfields Road | L | 0-2 | Fred Scotchbrook | Peter Proudfoot | G Watson (West Bridgford) |
| 1926/27 | Football League (2) | 5 February 1927 | Molineux | W | 5-0 | Fred Scotchbrook | Peter Proudfoot | G Watson (West Bridgford) |
| 1927/28 | Football League (2) | 24 December 1927 | Molineux | W | 5-3 | Major Frank Buckley | Peter Proudfoot | J Pennington (Reading) |
| 1927/28 | Football League (2) | 5 May 1928 | Millfields Road | D | 0-0 | Major Frank Buckley | Peter Proudfoot | J Pennington (Reading) |
| 1928/29 | Football League (2) | 15 December 1928 | Molineux | W | 3-2 | Major Frank Buckley | Peter Proudfoot | W Phipps (West Bromwich) |
| 1928/29 | Football League (2) | 27 April 1929 | Millfields Road | L | 0-2 | Major Frank Buckley | Peter Proudfoot | W Forshaw (Liverpool) |
As Leyton Orient
| 1962/63 | Football League (1) | 24 November 1962 | Brisbane Road | W | 4-0 | Stan Cullis | Johnny Carey | R Hamer (Bristol) |
| 1962/63 | Football League (1) | 30 March 1963 | Molineux | W | 2-1 | Stan Cullis | Johnny Carey | J Parkinson (Blackburn) |
| 1965/66 | Football League (2) | 9 October 1965 | Brisbane Road | W | 3-0 | Andy Beattie © | Dave Sexton | T Dawes (Norwich) |
| 1965/66 | Football League (2) | 1 January 1966 | Molineux | W | 2-1 | Andy Beattie © | Les Gore © | C Duxbury (Preston) |
As Orient
| 1972/73 | FL Cup | 5 September 1972 | Molineux | W | 2-1 | Bill McGarry | George Petchey | AW Jones (Ormskirk) |
| 1976/77 | Football League (2) | 27 November 1976 | Brisbane Road | W | 4-2 | Sammy Chung | George Petchey | R Challis (Tonbridge) |
| 1976/77 | Football League (2) | 23 April 1977 | Molineux | W | 1-0 | Sammy Chung | George Petchey | E Garner (Maghull, Liverpool) |
| 1986/87 | Football League (4) | 25 October 1986 | Molineux | W | 3-1 | Graham Turner | Frank Clarke | K Morton (Burton St Edmunds) |
| 1986/87 | Football League (4) | 7 March 1987 | Brisbane Road | L | 1-3 | Graham Turner | Frank Clarke | I Borrett (Harleston) |
As Leyton Orient
| 1987/88 | Football League (4) | 19 December 1987 | Molineux | W | 2-0 | Graham Turner | Frank Clarke | K Walmsley (Blackpool) |
| 1987/88 | Football League (4) | 7 May 1988 | Brisbane Road | W | 2-0 | Graham Turner | Frank Clarke | P Durkin (Portland, Dorset) |
| 2013/14 | Football League (L1) | 29 December 2013 | Molineux | D | 1-1 | Kenny Jackett | Russell Slade | D Coote (Nottingham) |
| 2013/14 | Football League (L1) | 21 April 2014 | Brisbane Road | W | 3-1 | Kenny Jackett | Russell Slade | N Swarbrick (Preston) |
