| 1. Round | 11/08/2018 | Newcastle United | - | Tottenham Hotspur | 1:2 | ||||
| 2. Round | 18/08/2018 | Tottenham Hotspur | - | Fulham FC | 3:1 | ||||
| 3. Round | 27/08/2018 | Manchester United | - | Tottenham Hotspur | 0:3 | ||||
| 4. Round | 02/09/2018 | Watford FC | - | Tottenham Hotspur | 2:1 |  |
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| 5. Round | 15/09/2018 | Tottenham Hotspur | - | Liverpool FC | 1:2 | ||||
| 6. Round | 22/09/2018 | Brighton & Hove Albion | - | Tottenham Hotspur | 1:2 | ||||
| 7. Round | 29/09/2018 | Huddersfield Town | - | Tottenham Hotspur | 0:2 | ||||
| 9. Round | 20/10/2018 | West Ham United | - | Tottenham Hotspur | 0:1 | ||||
| 10. Round | 29/10/2018 | Tottenham Hotspur | - | Manchester City | 0:1 | ||||
| 11. Round | 03/11/2018 | Wolverhampton Wanderers | - | Tottenham Hotspur | 2:3 |
Belgium
