| 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 | 4/12/2019 | 2-1 v Aston VillaChelsea 2-1 Aston Villa | Premier League |
| 21 | 7/12/2019 | 1-3 v EvertonEverton 3-1 Chelsea | Premier League |
| 22 | 10/12/2019 | 2-1 v LilleChelsea 2-1 Lille | UEFA Champions League Group H |
| 23 | 14/12/2019 | 0-1 v AFC BournemouthChelsea 0-1 AFC Bournemouth | Premier League |
| 24 | 22/12/2019 | 2-0 v Tottenham HotspurTottenham Hotspur 0-2 Chelsea | Premier League |
| 25 | 26/12/2019 | 0-2 v SouthamptonChelsea 0-2 Southampton | Premier League |
| 26 | 29/12/2019 | 2-1 v ArsenalArsenal 1-2 Chelsea | Premier League |
| 27 | 1/1/2020 | 1-1 v Brighton & Hove AlbionBrighton & Hove Albion 1-1 Chelsea | Premier League |
| 28 | 11/1/2020 | 3-0 v BurnleyChelsea 3-0 Burnley | Premier League |
| 29 | 18/1/2020 | 0-1 v Newcastle UnitedNewcastle United 1-0 Chelsea | Premier League |
| 30 | 21/1/2020 | 2-2 v ArsenalChelsea 2-2 Arsenal | Premier League |
| 31 | 1/2/2020 | 2-2 v Leicester CityLeicester City 2-2 Chelsea | Premier League |
| 32 | 22/2/2020 | 2-1 v Tottenham HotspurChelsea 2-1 Tottenham Hotspur | Premier League |
| 33 | 25/2/2020 | 0-3 v Bayern MunichChelsea 0-3 Bayern Munich | UEFA Champions League Round of 16 |
