| 1 | 11/8/2019 | 0-4 v Manchester UnitedManchester United 4-0 Chelsea | Premier League |
| 2 | 18/8/2019 | 1-1 v Leicester CityChelsea 1-1 Leicester City | Premier League |
| 3 | 24/8/2019 | 3-2 v Norwich CityNorwich City 2-3 Chelsea | Premier League |
| 4 | 31/8/2019 | 2-2 v Sheffield UnitedChelsea 2-2 Sheffield United | Premier League |
| 5 | 14/9/2019 | 5-2 v Wolverhampton WanderersWolverhampton Wanderers 2-5 Chelsea | Premier League |
| 6 | 17/9/2019 | 0-1 v ValenciaChelsea 0-1 Valencia | UEFA Champions League Group H |
| 7 | 22/9/2019 | 1-2 v LiverpoolChelsea 1-2 Liverpool | Premier League |
| 8 | 25/9/2019 | 7-1 v Grimsby TownChelsea 7-1 Grimsby Town | Carabao Cup Third Round |
| 9 | 28/9/2019 | 2-0 v Brighton & Hove AlbionChelsea 2-0 Brighton & Hove Albion | Premier League |
| 10 | 2/10/2019 | 2-1 v LilleLille 1-2 Chelsea | UEFA Champions League Group H |
| 11 | 6/10/2019 | 4-1 v SouthamptonSouthampton 1-4 Chelsea | Premier League |
| 12 | 19/10/2019 | 1-0 v Newcastle UnitedChelsea 1-0 Newcastle United | Premier League |
| 13 | 23/10/2019 | 1-0 v AjaxAjax 0-1 Chelsea | UEFA Champions League Group H |
| 14 | 26/10/2019 | 4-2 v BurnleyBurnley 2-4 Chelsea | Premier League |
| 15 | 2/11/2019 | 2-1 v WatfordWatford 1-2 Chelsea | Premier League |
| 16 | 5/11/2019 | 4-4 v AjaxChelsea 4-4 Ajax | UEFA Champions League Group H |
| 17 | 9/11/2019 | 2-0 v Crystal PalaceChelsea 2-0 Crystal Palace | Premier League |
| 18 | 23/11/2019 | 1-2 v Manchester CityManchester City 2-1 Chelsea | Premier League |
| 19 | 27/11/2019 | 2-2 v ValenciaValencia 2-2 Chelsea | UEFA Champions League Group H |
| 20 | 30/11/2019 | 0-1 v West Ham UnitedChelsea 0-1 West Ham United | Premier League |
| 21 | 4/12/2019 | 2-1 v Aston VillaChelsea 2-1 Aston Villa | Premier League |
