| 1 | Sat 17 Aug 2019 | 2-2 v Manchester CityManchester City 2-2 Tottenham Hotspur | Premier League |
| 2 | Sun 25 Aug 2019 | 0-1 v Newcastle UnitedTottenham Hotspur 0-1 Newcastle United | Premier League |
| 3 | Sun 1 Sep 2019 | 2-2 v ArsenalArsenal 2-2 Tottenham Hotspur | Premier League |
| 4 | Tue 22 Oct 2019 | 5-0 v Red Star BelgradeTottenham Hotspur 5-0 Red Star Belgrade | UEFA Champions League Group B |
| 5 | Sun 27 Oct 2019 | 1-2 v LiverpoolLiverpool 2-1 Tottenham Hotspur | Premier League |
| 6 | Wed 6 Nov 2019 | 4-0 v Red Star BelgradeRed Star Belgrade 0-4 Tottenham Hotspur | UEFA Champions League Group B |
| 7 | Sat 9 Nov 2019 | 1-1 v Sheffield UnitedTottenham Hotspur 1-1 Sheffield United | Premier League |
| 8 | Tue 26 Nov 2019 | 4-2 v OlympiakosTottenham Hotspur 4-2 Olympiakos | UEFA Champions League Group B |
| 9 | Sat 30 Nov 2019 | 3-2 v AFC BournemouthTottenham Hotspur 3-2 AFC Bournemouth | Premier League |
| 10 | Wed 4 Dec 2019 | 1-2 v Manchester UnitedManchester United 2-1 Tottenham Hotspur | Premier League |
| 11 | Wed 11 Dec 2019 | 1-3 v Bayern MunichBayern Munich 3-1 Tottenham Hotspur | UEFA Champions League Group B |
| 12 | Thu 26 Dec 2019 | 2-1 v Brighton & Hove AlbionTottenham Hotspur 2-1 Brighton & Hove Albion | Premier League |
| 13 | Sat 28 Dec 2019 | 2-2 v Norwich CityNorwich City 2-2 Tottenham Hotspur | Premier League |
| 14 | Wed 1 Jan 2020 | 0-1 v SouthamptonSouthampton 1-0 Tottenham Hotspur | Premier League |
| 15 | Sun 5 Jan 2020 | 1-1 v MiddlesbroughMiddlesbrough 1-1 Tottenham Hotspur | Emirates FA Cup Third Round |
| 16 | Tue 14 Jan 2020 | 2-1 v MiddlesbroughTottenham Hotspur 2-1 Middlesbrough | Emirates FA Cup Third Round Replay |
| 17 | Sat 18 Jan 2020 | 0-0 v WatfordWatford 0-0 Tottenham Hotspur | Premier League |
| 18 | Wed 22 Jan 2020 | 2-1 v Norwich CityTottenham Hotspur 2-1 Norwich City | Premier League |
| 19 | Sat 25 Jan 2020 | 1-1 v SouthamptonSouthampton 1-1 Tottenham Hotspur | Emirates FA Cup Fourth Round |
| 20 | Sun 16 Feb 2020 | 3-2 v Aston VillaAston Villa 2-3 Tottenham Hotspur | Premier League |
| 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 | Fri 19 Jun 2020 | 181-1 v Manchester UnitedTottenham Hotspur 1-1 Manchester United | Premier League |
| 28 | Tue 23 Jun 2020 | 182-0 v West Ham UnitedTottenham Hotspur 2-0 West Ham United | Premier League |
| 29 | Thu 2 Jul 2020 | 181-3 v Sheffield UnitedSheffield United 3-1 Tottenham Hotspur | Premier League |
| 30 | Mon 6 Jul 2020 | 181-0 v EvertonTottenham Hotspur 1-0 Everton | Premier League |
| 31 | Thu 9 Jul 2020 | 180-0 v AFC BournemouthAFC Bournemouth 0-0 Tottenham Hotspur | Premier League |
| 32 | Sun 12 Jul 2020 | 18 2-1 v ArsenalTottenham Hotspur 2-1 Arsenal | Premier League |
| 33 | Wed 15 Jul 2020 | 183-1 v Newcastle UnitedNewcastle United 1-3 Tottenham Hotspur | Premier League |
| 34 | Sun 19 Jul 2020 | 183-0 v Leicester CityTottenham Hotspur 3-0 Leicester City | Premier League |
| 35 | Sun 26 Jul 2020 | 181-1 v Crystal PalaceCrystal Palace 1-1 Tottenham Hotspur | Premier League |
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