| 1 | Sat 31 Aug 2019 | 2-2 v Sheffield UnitedChelsea 2-2 Sheffield United | Premier League |
| 2 | Sat 14 Sep 2019 | 5-2 v Wolverhampton WanderersWolverhampton Wanderers 2-5 Chelsea | Premier League |
| 3 | Tue 17 Sep 2019 | 0-1 v ValenciaChelsea 0-1 Valencia | UEFA Champions League Group H |
| 4 | Sun 22 Sep 2019 | 1-2 v LiverpoolChelsea 1-2 Liverpool | Premier League |
| 5 | Wed 25 Sep 2019 | 7-1 v Grimsby TownChelsea 7-1 Grimsby Town | Carabao Cup Third Round |
| 6 | Sat 28 Sep 2019 | 2-0 v Brighton & Hove AlbionChelsea 2-0 Brighton & Hove Albion | Premier League |
| 7 | Wed 2 Oct 2019 | 2-1 v LilleLille 1-2 Chelsea | UEFA Champions League Group H |
| 8 | Sun 6 Oct 2019 | 4-1 v SouthamptonSouthampton 1-4 Chelsea | Premier League |
| 9 | Wed 23 Oct 2019 | 1-0 v AjaxAjax 0-1 Chelsea | UEFA Champions League Group H |
| 10 | Sat 2 Nov 2019 | 2-1 v WatfordWatford 1-2 Chelsea | Premier League |
| 11 | Tue 5 Nov 2019 | 4-4 v AjaxChelsea 4-4 Ajax | UEFA Champions League Group H |
| 12 | Sat 9 Nov 2019 | 2-0 v Crystal PalaceChelsea 2-0 Crystal Palace | Premier League |
| 13 | Sat 23 Nov 2019 | 1-2 v Manchester CityManchester City 2-1 Chelsea | Premier League |
| 14 | Wed 27 Nov 2019 | 2-2 v ValenciaValencia 2-2 Chelsea | UEFA Champions League Group H |
| 15 | Wed 4 Dec 2019 | 2-1 v Aston VillaChelsea 2-1 Aston Villa | Premier League |
| 16 | Sat 7 Dec 2019 | 1-3 v EvertonEverton 3-1 Chelsea | Premier League |
| 17 | Tue 10 Dec 2019 | 2-1 v LilleChelsea 2-1 Lille | UEFA Champions League Group H |
| 18 | Sat 14 Dec 2019 | 0-1 v AFC BournemouthChelsea 0-1 AFC Bournemouth | Premier League |
| 19 | Sun 22 Dec 2019 | 2-0 v Tottenham HotspurTottenham Hotspur 0-2 Chelsea | Premier League |
| 20 | Sun 5 Jan 2020 | 2-0 v Nottingham ForestChelsea 2-0 Nottingham Forest | Emirates FA Cup Third Round |
| 21 | Sat 18 Jan 2020 | 0-1 v Newcastle UnitedNewcastle United 1-0 Chelsea | Premier League |
| 22 | Tue 21 Jan 2020 | 2-2 v ArsenalChelsea 2-2 Arsenal | Premier League |
| 23 | Sat 25 Jan 2020 | 2-1 v Hull CityHull City 1-2 Chelsea | Emirates FA Cup Fourth Round |
| 24 | Mon 17 Feb 2020 | 0-2 v Manchester UnitedChelsea 0-2 Manchester United | Premier League |
| 25 | Sat 29 Feb 2020 | 2-2 v AFC BournemouthAFC Bournemouth 2-2 Chelsea | Premier League |
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