| 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) |
| 14.12.20162016-12-14 20:45:00 | 20:45 | Premier League | 16. R | Sunderland - Chelsea | -:- |
| 11.12.20162016-12-11 13:00:00 | 13:00 | Premier League | 15. R | Chelsea - West Bromwich | -:- |
| 3.12.20162016-12-3 13:30:00 | 13:30 | Premier League | 14. R | Manchester City - Chelsea | 1:3 (1:0) |
| 26.11.20162016-11-26 18:30:00 | 18:30 | Premier League | 13. R | Chelsea - Tottenham Hotspur | 2:1 (1:1) |
| 20.11.20162016-11-20 17:00:00 | 17:00 | Premier League | 12. R | Middlesbrough - Chelsea | 0:1 (0:1) |
| 5.11.20162016-11-5 18:30:00 | 18:30 | Premier League | 11. R | Chelsea - Everton | 5:0 (3:0) |
| 30.10.20162016-10-30 17:00:00 | 17:00 | Premier League | 10. R | Southampton - Chelsea | 0:2 (0:1) |
| 26.10.20162016-10-26 20:45:00 | 20:45 | EFL Cup | 4. R | West Ham United - Chelsea | 2:1 (1:0) |