| 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) |
| 8.12.20162016-12-8 19:00:00 | 19:00 | Europa League Grp. B | 6. R | APOEL Nikosia - Olympiacos | -:- |
| 24.11.20162016-11-24 21:05:00 | 21:05 | Europa League Grp. B | 5. R | Olympiacos - BSC Young Boys | 1:1 (0:0) |
| 3.11.20162016-11-3 17:00:00 | 17:00 | Europa League Grp. B | 4. R | FC Astana - Olympiacos | 1:1 (1:1) |
| 20.10.20162016-10-20 21:05:00 | 21:05 | Europa League Grp. B | 3. R | Olympiacos - FC Astana | 4:1 (3:0) |
| 29.9.20162016-9-29 21:05:00 | 21:05 | Europa League Grp. B | 2. R | Olympiacos - APOEL Nikosia | 0:1 (0:1) |
| 15.9.20162016-9-15 19:00:00 | 19:00 | Europa League Grp. B | 1. R | BSC Young Boys - Olympiacos | 0:1 (0:1) |
| 25.8.20162016-8-25 20:45:00 | 20:45 | Europa League Qualification | Finale | Olympiacos - Arouca | 2:1 (0:0) |