| 1 | 17/8/2019 | 2-2 v Manchester CityManchester City 2-2 Tottenham Hotspur | Premier League |
| 2 | 25/8/2019 | 0-1 v Newcastle UnitedTottenham Hotspur 0-1 Newcastle United | Premier League |
| 3 | 1/9/2019 | 2-2 v ArsenalArsenal 2-2 Tottenham Hotspur | Premier League |
| 4 | 22/10/2019 | 5-0 v Red Star BelgradeTottenham Hotspur 5-0 Red Star Belgrade | UEFA Champions League Group B |
| 5 | 27/10/2019 | 1-2 v LiverpoolLiverpool 2-1 Tottenham Hotspur | Premier League |
| 6 | 3/11/2019 | 1-1 v EvertonEverton 1-1 Tottenham Hotspur | Premier League |
| 7 | 6/11/2019 | 4-0 v Red Star BelgradeRed Star Belgrade 0-4 Tottenham Hotspur | UEFA Champions League Group B |
| 8 | 9/11/2019 | 1-1 v Sheffield UnitedTottenham Hotspur 1-1 Sheffield United | Premier League |
| 9 | 23/11/2019 | 3-2 v West Ham UnitedWest Ham United 2-3 Tottenham Hotspur | Premier League |
| 10 | 26/11/2019 | 4-2 v OlympiakosTottenham Hotspur 4-2 Olympiakos | UEFA Champions League Group B |
| 11 | 30/11/2019 | 3-2 v AFC BournemouthTottenham Hotspur 3-2 AFC Bournemouth | Premier League |
| 12 | 4/12/2019 | 1-2 v Manchester UnitedManchester United 2-1 Tottenham Hotspur | Premier League |
| 13 | 7/12/2019 | 5-0 v BurnleyTottenham Hotspur 5-0 Burnley | Premier League |
