| 6.12.20162016-12-6 20:45:00 | 20:45 | EFL Trophy Final Stage | 2. R | Southend United - Oxford United | -:- |
| 8.11.20162016-11-8 20:45:00 | 20:45 | EFL Trophy Southern Group G | 3. R | Stevenage - Southend United | 4:0 (2:0) |
| 4.11.20162016-11-4 20:45:00 | 20:45 | FA Cup | 1. R | Millwall - Southend United | 1:0 (0:0) |
| 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 | Southend United - Brighton & Hove Albion Academy | 2:0 (1:0) |
| 9.8.20162016-8-9 20:45:00 | 20:45 | EFL Cup | 1. R | Southend United - Gillingham | 1:3 (1:0) |
| 8.12.20152015-12-8 20:45:00 | 20:45 | Johnstones Paint Trophy | 1/4 | Southend United - Millwall | 0:2 (0:1) |
| 9.8.20162016-8-9 20:45:00 | 20:45 | EFL Cup | 1. R | Barnsley - Northampton Town | 1:2 (1:0) |
| 3.4.20162016-4-3 15:30:00 | 15:30 | Johnstones Paint Trophy | Finale | Barnsley - Oxford United | 3:2 (0:1) |
| 4.2.20162016-2-4 20:45:00 | 20:45 | Johnstones Paint Trophy | 1/2 | Fleetwood Town - Barnsley | 3:5 (0:0) |
| 9.1.20162016-1-9 16:00:00 | 16:00 | Johnstones Paint Trophy | 1/2 | Barnsley - Fleetwood Town | 1:1 (0:0) |
| 5.12.20152015-12-5 16:00:00 | 16:00 | Johnstones Paint Trophy | 1/4 | Wigan Athletic - Barnsley | 4:6 (0:1) |
| 10.11.20152015-11-10 20:45:00 | 20:45 | Johnstones Paint Trophy | 1/8 | Barnsley - York City | 2:1 (0:1) |