Leyton Orient have played Maidstone United 2 times in competitive football, winning 1, drawing 1 and losing 0, first meeting on 29 Aug 1990 and most recently on 4 Sep 1990. Every meeting is listed below.
| Date | Season | Competition | Venue | Opponent | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 29 Aug 1990 | 1990–91 | League Cup | A | Maidstone United | 2–2 | ||
| 4 Sep 1990 | 1990–91 | League Cup | H | Maidstone United | 4–1 |
All Leyton Orient head-to-head records · Leyton Orient season by season