| 1 | Sun 11 Aug 2019 | 0-4 v Manchester UnitedManchester United 4-0 Chelsea | Premier League |
| 2 | Sun 18 Aug 2019 | 1-1 v Leicester CityChelsea 1-1 Leicester City | Premier League |
| 3 | Sat 24 Aug 2019 | 3-2 v Norwich CityNorwich City 2-3 Chelsea | Premier League |
| 4 | Sat 31 Aug 2019 | 2-2 v Sheffield UnitedChelsea 2-2 Sheffield United | Premier League |
| 5 | Sat 14 Sep 2019 | 5-2 v Wolverhampton WanderersWolverhampton Wanderers 2-5 Chelsea | Premier League |
| 6 | Tue 17 Sep 2019 | 0-1 v ValenciaChelsea 0-1 Valencia | UEFA Champions League Group H |
| 7 | Sun 22 Sep 2019 | 1-2 v LiverpoolChelsea 1-2 Liverpool | Premier League |
| 8 | Sat 28 Sep 2019 | 2-0 v Brighton & Hove AlbionChelsea 2-0 Brighton & Hove Albion | Premier League |
| 9 | Wed 2 Oct 2019 | 2-1 v LilleLille 1-2 Chelsea | UEFA Champions League Group H |
| 10 | Sun 6 Oct 2019 | 4-1 v SouthamptonSouthampton 1-4 Chelsea | Premier League |
| 11 | Fri 11 Oct 2019 | 1-2 v Czech RepublicCzech Republic 2-1 England | European Championship Qualification Group A |
| 12 | Mon 14 Oct 2019 | 6-0 v BulgariaBulgaria 0-6 England | European Championship Qualification Group A |
| 13 | Sat 19 Oct 2019 | 1-0 v Newcastle UnitedChelsea 1-0 Newcastle United | Premier League |
| 14 | Wed 23 Oct 2019 | 1-0 v AjaxAjax 0-1 Chelsea | UEFA Champions League Group H |
| 15 | Sat 26 Oct 2019 | 4-2 v BurnleyBurnley 2-4 Chelsea | Premier League |
| 16 | Sat 2 Nov 2019 | 2-1 v WatfordWatford 1-2 Chelsea | Premier League |
| 17 | Tue 5 Nov 2019 | 4-4 v AjaxChelsea 4-4 Ajax | UEFA Champions League Group H |
| 18 | Sat 9 Nov 2019 | 2-0 v Crystal PalaceChelsea 2-0 Crystal Palace | Premier League |
| 19 | Thu 14 Nov 2019 | 7-0 v MontenegroEngland 7-0 Montenegro | European Championship Qualification Group A |
| 20 | Sun 17 Nov 2019 | 4-0 v KosovoKosovo 0-4 England | European Championship Qualification Group A |
| 21 | Sat 23 Nov 2019 | 1-2 v Manchester CityManchester City 2-1 Chelsea | Premier League |
| 22 | Wed 27 Nov 2019 | 2-2 v ValenciaValencia 2-2 Chelsea | UEFA Champions League Group H |
| 23 | Sat 30 Nov 2019 | 0-1 v West Ham UnitedChelsea 0-1 West Ham United | Premier League |
| 24 | Wed 4 Dec 2019 | 2-1 v Aston VillaChelsea 2-1 Aston Villa | Premier League |
| 25 | Sat 7 Dec 2019 | 1-3 v EvertonEverton 3-1 Chelsea | Premier League |
| 26 | Tue 10 Dec 2019 | 2-1 v LilleChelsea 2-1 Lille | UEFA Champions League Group H |
| 27 | Sat 14 Dec 2019 | 0-1 v AFC BournemouthChelsea 0-1 AFC Bournemouth | Premier League |
| 28 | Sun 22 Dec 2019 | 2-0 v Tottenham HotspurTottenham Hotspur 0-2 Chelsea | Premier League |
| 29 | Thu 26 Dec 2019 | 0-2 v SouthamptonChelsea 0-2 Southampton | Premier League |
| 30 | Sun 29 Dec 2019 | 2-1 v ArsenalArsenal 1-2 Chelsea | Premier League |
| 31 | Wed 1 Jan 2020 | 1-1 v Brighton & Hove AlbionBrighton & Hove Albion 1-1 Chelsea | Premier League |
| 32 | Sun 5 Jan 2020 | 2-0 v Nottingham ForestChelsea 2-0 Nottingham Forest | Emirates FA Cup Third Round |
| 33 | Sat 11 Jan 2020 | 3-0 v BurnleyChelsea 3-0 Burnley | Premier League |
| 34 | Sat 18 Jan 2020 | 0-1 v Newcastle UnitedNewcastle United 1-0 Chelsea | Premier League |
| 35 | Tue 21 Jan 2020 | 2-2 v ArsenalChelsea 2-2 Arsenal | Premier League |
| 36 | Sat 25 Jan 2020 | 2-1 v Hull CityHull City 1-2 Chelsea | Emirates FA Cup Fourth Round |
| 37 | Sat 1 Feb 2020 | 2-2 v Leicester CityLeicester City 2-2 Chelsea | Premier League |
| 38 | Mon 17 Feb 2020 | 0-2 v Manchester UnitedChelsea 0-2 Manchester United | Premier League |
| 39 | Sat 22 Feb 2020 | 2-1 v Tottenham HotspurChelsea 2-1 Tottenham Hotspur | Premier League |
| 40 | Tue 25 Feb 2020 | 0-3 v Bayern MunichChelsea 0-3 Bayern Munich | UEFA Champions League Round of 16 |
| 41 | Sat 29 Feb 2020 | 2-2 v AFC BournemouthAFC Bournemouth 2-2 Chelsea | Premier League |
| 42 | Tue 3 Mar 2020 | 2-0 v LiverpoolChelsea 2-0 Liverpool | Emirates FA Cup Fifth Round |
| 43 | Sun 8 Mar 2020 | 4-0 v EvertonChelsea 4-0 Everton | Premier League |
| 44 | Sun 21 Jun 2020 | 192-1 v Aston VillaAston Villa 1-2 Chelsea | Premier League |
| 45 | Thu 25 Jun 2020 | 192-1 v Manchester CityChelsea 2-1 Manchester City | Premier League |
| 46 | Sun 28 Jun 2020 | 191-0 v Leicester CityLeicester City 0-1 Chelsea | Emirates FA Cup Sixth Round |
| 47 | Wed 1 Jul 2020 | 192-3 v West Ham UnitedWest Ham United 3-2 Chelsea | Premier League |
| 48 | Sat 4 Jul 2020 | 193-0 v WatfordChelsea 3-0 Watford | Premier League |
| 49 | Tue 7 Jul 2020 | 193-2 v Crystal PalaceCrystal Palace 2-3 Chelsea | Premier League |
| 50 | Sat 11 Jul 2020 | 190-3 v Sheffield UnitedSheffield United 3-0 Chelsea | Premier League |
| 51 | Sun 19 Jul 2020 | 193-1 v Manchester UnitedManchester United 1-3 Chelsea | Emirates FA Cup Semi Final |
| 52 | Wed 22 Jul 2020 | 193-5 v LiverpoolLiverpool 5-3 Chelsea | Premier League |
| 53 | Sun 26 Jul 2020 | 192-0 v Wolverhampton WanderersChelsea 2-0 Wolverhampton Wanderers | Premier League |
| 54 | Sat 1 Aug 2020 | 19 1-2 v ArsenalArsenal 2-1 Chelsea | Emirates FA Cup Final |
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