Head to Head
| England National League | 2019/02/16 15:00 | Leyton Orient v Maidenhead Utd | W | 0-1 |
| England National League | 2018/10/06 14:00 | Maidenhead Utd v Leyton Orient | L | 0-2 |
| England National League | 2018/04/24 18:45 | Leyton Orient v Maidenhead Utd | W | 0-1 |
| England National League | 2017/08/28 14:00 | Maidenhead Utd v Leyton Orient | L | 0-1 |
Home History
| England National League | 2021/05/29 11:30 | Boreham Wood v Maidenhead Utd | W | 1-4 |
| England National League | 2021/05/25 18:45 | Barnet v Maidenhead Utd | L | 2-0 |
| England National League | 2021/05/22 14:00 | Maidenhead Utd v Halifax | L | 1-2 |
| England National League | 2021/05/18 18:45 | Yeovil v Maidenhead Utd | D | 0-0 |
| England National League | 2021/05/15 14:00 | Maidenhead Utd v Sutton Utd | L | 0-3 |
| England National League | 2021/05/11 18:45 | Maidenhead Utd v Notts County | L | 0-4 |
| England National League | 2021/05/08 14:00 | Hartlepool v Maidenhead Utd | W | 2-4 |
| England National League | 2021/05/03 14:00 | Maidenhead Utd v Wrexham | D | 2-2 |
Away History
| Elite Club Friendlies | 2021/07/17 14:00 | Leyton Orient v Tottenham | D | 1-1 |
| Elite Club Friendlies | 2021/07/13 18:00 | Leyton Orient v West Ham | D | 0-0 |
| UK Friendlies | 2021/07/13 18:00 | Leyton Orient v West Ham XI | D | 0-0 |
| Club Friendly List | 2021/07/06 16:00 | Dundee v Leyton Orient | L | 3-0 |
| England League 2 | 2021/05/08 15:00 | Salford City v Leyton Orient | L | 3-0 |
| England League 2 | 2021/05/01 14:00 | Leyton Orient v Carlisle | L | 2-3 |
| England League 2 | 2021/04/24 14:00 | Southend v Leyton Orient | L | 2-1 |
| England League 2 | 2021/04/20 18:00 | Leyton Orient v Cambridge Utd | L | 2-4 |