| 8.11.20162016-11-8 20:45:00 | 20:45 | EFL Trophy Southern Group G | 3. R |
Brighton & Hove Albion Academy - Leyton Orient
| 1:0 (1:0) | The American Express Community StadiumVillage WayBrighton,BN1 9BLGB |
| 6.11.20162016-11-6 15:05:00 | 15:05 | FA Cup | 1. R |
Sheffield United - Leyton Orient
| 6:0 (3:0) | Bramall LaneBramall LaneSheffield,S2 4SUGB |
| 4.10.20162016-10-4 20:45:00 | 20:45 | EFL Trophy Southern Group G | 2. R |
Southend United - Leyton Orient
| 1:0 (0:0) |
| 30.8.20162016-8-30 20:45:00 | 20:45 | EFL Trophy Southern Group G | 1. R |
Leyton Orient - Stevenage
| 3:1 (1:0) | Matchroom StadiumBrisbane Road, LeytonLondon,E10 5NFGB |
| 9.8.20162016-8-9 20:45:00 | 20:45 | EFL Cup | 1. R |
Leyton Orient - Fulham
| 2:3 (0:1) | Matchroom StadiumBrisbane Road, LeytonLondon,E10 5NFGB |
| 15.12.20152015-12-15 20:45:00 | 20:45 | FA Cup | 2. R |
Scunthorpe United - Leyton Orient
| 3:0 (0:0) | Glanford ParkDoncaster RoadScunthorpe,DN15 8TDGB |
