| 1 | Sat 10 Aug 2019 | 3-1 v Aston VillaTottenham Hotspur 3-1 Aston Villa | Premier League |
| 2 | Sat 17 Aug 2019 | 2-2 v Manchester CityManchester City 2-2 Tottenham Hotspur | Premier League |
| 3 | Sat 14 Sep 2019 | 4-0 v Crystal PalaceTottenham Hotspur 4-0 Crystal Palace | Premier League |
| 4 | Wed 18 Sep 2019 | 2-2 v OlympiakosOlympiakos 2-2 Tottenham Hotspur | UEFA Champions League Group B |
| 5 | Sat 21 Sep 2019 | 1-2 v Leicester CityLeicester City 2-1 Tottenham Hotspur | Premier League |
| 6 | Sat 28 Sep 2019 | 2-1 v SouthamptonTottenham Hotspur 2-1 Southampton | Premier League |
| 7 | Tue 1 Oct 2019 | 2-7 v Bayern MunichTottenham Hotspur 2-7 Bayern Munich | UEFA Champions League Group B |
| 8 | Sat 5 Oct 2019 | 0-3 v Brighton & Hove AlbionBrighton & Hove Albion 3-0 Tottenham Hotspur | Premier League |
| 9 | Sat 19 Oct 2019 | 1-1 v WatfordTottenham Hotspur 1-1 Watford | Premier League |
| 10 | Tue 22 Oct 2019 | 5-0 v Red Star BelgradeTottenham Hotspur 5-0 Red Star Belgrade | UEFA Champions League Group B |
| 11 | Sun 27 Oct 2019 | 1-2 v LiverpoolLiverpool 2-1 Tottenham Hotspur | Premier League |
| 12 | Sun 3 Nov 2019 | 1-1 v EvertonEverton 1-1 Tottenham Hotspur | Premier League |
| 13 | Wed 6 Nov 2019 | 4-0 v Red Star BelgradeRed Star Belgrade 0-4 Tottenham Hotspur | UEFA Champions League Group B |
| 14 | Sat 9 Nov 2019 | 1-1 v Sheffield UnitedTottenham Hotspur 1-1 Sheffield United | Premier League |
| 15 | Sat 30 Nov 2019 | 3-2 v AFC BournemouthTottenham Hotspur 3-2 AFC Bournemouth | Premier League |
| 16 | Wed 4 Dec 2019 | 1-2 v Manchester UnitedManchester United 2-1 Tottenham Hotspur | Premier League |
| 17 | Sun 22 Dec 2019 | 0-2 v ChelseaTottenham Hotspur 0-2 Chelsea | Premier League |
| 18 | Sat 28 Dec 2019 | 2-2 v Norwich CityNorwich City 2-2 Tottenham Hotspur | Premier League |
| 19 | Wed 1 Jan 2020 | 0-1 v SouthamptonSouthampton 1-0 Tottenham Hotspur | Premier League |
| 20 | Wed 5 Feb 2020 | 3-2 v SouthamptonTottenham Hotspur 3-2 Southampton | Emirates FA Cup Fourth Round Replay |
| 21 | Wed 19 Feb 2020 | 0-1 v RB LeipzigTottenham Hotspur 0-1 RB Leipzig | UEFA Champions League Round of 16 |
| 22 | Sat 22 Feb 2020 | 1-2 v ChelseaChelsea 2-1 Tottenham Hotspur | Premier League |
| 23 | Sun 1 Mar 2020 | 2-3 v Wolverhampton WanderersTottenham Hotspur 2-3 Wolverhampton Wanderers | Premier League |
| 24 | Wed 4 Mar 2020 | 1-1 v Norwich CityTottenham Hotspur 1-1 Norwich City | Emirates FA Cup Fifth Round |
| 25 | Sat 7 Mar 2020 | 1-1 v BurnleyBurnley 1-1 Tottenham Hotspur | Premier League |
| 26 | Tue 10 Mar 2020 | 0-3 v RB LeipzigRB Leipzig 3-0 Tottenham Hotspur | UEFA Champions League Round of 16 |
| 27 | Thu 2 Jul 2020 | 281-3 v Sheffield UnitedSheffield United 3-1 Tottenham Hotspur | Premier League |
| 28 | Thu 9 Jul 2020 | 28 0-0 v AFC BournemouthAFC Bournemouth 0-0 Tottenham Hotspur | Premier League |
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