Leyton Orient have played Macclesfield 18 times in competitive football, winning 6, drawing 4 and losing 8, first meeting on 4 Oct 1997 and most recently on 8 Feb 2020. Every meeting is listed below.
| Date | Season | Competition | Venue | Opponent | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 4 Oct 1997 | 1997–98 | Third Division | H | Macclesfield | 1–1 | ||
| 14 Feb 1998 | 1997–98 | Third Division | A | Macclesfield | 0–1 | ||
| 18 Dec 1999 | 1999–00 | Third Division | A | Macclesfield | 0–1 | ||
| 1 Apr 2000 | 1999–00 | Third Division | H | Macclesfield | 0–0 | ||
| 25 Nov 2000 | 2000–01 | Third Division | H | Macclesfield | 2–1 | ||
| 5 May 2001 | 2000–01 | Third Division | A | Macclesfield | 2–0 | ||
| 15 Dec 2001 | 2001–02 | Third Division | A | Macclesfield | 1–2 | ||
| 9 Mar 2002 | 2001–02 | Third Division | H | Macclesfield | 2–0 | ||
| 13 Aug 2002 | 2002–03 | Third Division | H | Macclesfield | 3–2 | ||
| 11 Mar 2003 | 2002–03 | Third Division | A | Macclesfield | 1–3 | ||
| 4 Oct 2003 | 2003–04 | Third Division | H | Macclesfield | 2–0 | ||
| 10 Apr 2004 | 2003–04 | Third Division | A | Macclesfield | 0–1 | ||
| 7 Aug 2004 | 2004–05 | League Two | H | Macclesfield | 1–3 | ||
| 19 Mar 2005 | 2004–05 | League Two | A | Macclesfield | 1–3 | ||
| 6 Aug 2005 | 2005–06 | League Two | H | Macclesfield | 2–1 | ||
| 26 Nov 2005 | 2005–06 | League Two | A | Macclesfield | 0–0 | ||
| 10 Aug 2019 | 2019–20 | League Two | A | Macclesfield | 0–3 | 2,167 | |
| 8 Feb 2020 | 2019–20 | League Two | H | Macclesfield | 1–1 | James Brophy 75 | 5,708 |
All Leyton Orient head-to-head records · Leyton Orient season by season