[4] Tottenham 5-0 Roter Stern Belgrad [2] 2019-10-22 19:00
Stadion: Tottenham Hotspur Stadium Round: 3
Schiedsrichter: Marco Guida Home Manager: Mauricio Pochettino Away Manager: Vladan Milojevic
Home History
| England - Premier League | 2019/10/19 14:00 | Tottenham v Watford | D | 1-1 |
| England - Premier League | 2019/10/05 11:30 | Brighton v Tottenham | L | 3-0 |
| UEFA Champions League | 2019/10/01 19:00 | Tottenham v Bayern München | L | 2-7 |
| England - Premier League | 2019/09/28 14:00 | Tottenham v Southampton | W | 2-1 |
| England - EFL Cup | 2019/09/24 18:45 | Colchester v Tottenham | L | 4-3 |
| England - Premier League | 2019/09/21 11:30 | Leicester v Tottenham | L | 2-1 |
| UEFA Champions League | 2019/09/18 16:55 | Olympiakos v Tottenham | D | 2-2 |
| England - Premier League | 2019/09/14 14:00 | Tottenham v Crystal Palace | W | 4-0 |
Away History
| Serbien - Super Liga | 2019/10/18 18:00 | Roter Stern Belgrad v Rad Belgrade | W | 3-1 |
| Serbien - Pokal | 2019/10/10 13:00 | FC Trepca v Roter Stern Belgrad | W | 0-8 |
| Serbien - Super Liga | 2019/10/06 14:00 | FK Napredak v Roter Stern Belgrad | W | 0-1 |
| UEFA Champions League | 2019/10/01 19:00 | Roter Stern Belgrad v Olympiakos | W | 3-1 |
| Serbien - Super Liga | 2019/09/28 17:00 | Roter Stern Belgrad v FK Macva Sabac | W | 3-1 |
| Serbien - Super Liga | 2019/09/25 17:00 | FK Vozdovac v Roter Stern Belgrad | W | 1-3 |
| Serbien - Super Liga | 2019/09/22 16:00 | Partizan Belgrad v Roter Stern Belgrad | L | 2-0 |
| UEFA Champions League | 2019/09/18 19:00 | Bayern München v Roter Stern Belgrad | L | 3-0 |