Home History
| Club Friendly List | 2016/07/25 18:45 | Cheltenham v Bristol City | L | 1-2 |
| Club Friendly List | 2016/07/19 18:45 | Cheltenham v Barnsley | L | 1-3 |
| Club Friendly List | 2016/07/14 18:45 | Cirencester v Cheltenham | W | 0-3 |
| England National League | 2016/04/30 16:30 | Cheltenham v Lincoln City | W | 3-1 |
| England National League | 2016/04/23 14:00 | Macclesfield v Cheltenham | W | 0-1 |
| England National League | 2016/04/16 14:00 | Cheltenham v Halifax | W | 2-0 |
| England National League | 2016/04/09 14:00 | Guiseley v Cheltenham | W | 0-2 |
| England National League | 2016/04/01 18:45 | Cheltenham v Grimsby | W | 3-1 |
Away History
| Club Friendly List | 2016/07/26 18:45 | Dag & Red v Leyton Orient | W | 1-2 |
| Club Friendly List | 2016/07/12 18:45 | Wealdstone v Leyton Orient | W | 1-2 |
| England League 2 | 2016/05/07 14:00 | Yeovil v Leyton Orient | W | 0-1 |
| England League 2 | 2016/04/30 14:00 | Leyton Orient v Mansfield | W | 1-0 |
| England League 2 | 2016/04/23 14:00 | AFC Wimbledon v Leyton Orient | L | 1-0 |
| England League 2 | 2016/04/19 18:45 | Leyton Orient v Plymouth | L | 1-3 |
| England League 2 | 2016/04/16 14:00 | Leyton Orient v Dag & Red | W | 3-2 |
| England League 2 | 2016/04/09 14:00 | Barnet v Leyton Orient | L | 3-0 |