Shkendija Tetovo 1-3 Tottenham 2020-09-24 18:00
Stadium: Nacional Arena Todor Proeski Round: 16
Referee: Ali Palabiyik Home Manager: Erhan Selimi Away Manager: Jose Mourinho
Home History
| North Macedonia First League | 2020/09/20 13:30 | Shkendija Tetovo v AP Brera Strumica | W | 2-1 |
| UEFA Europa League Qualifying | 2020/09/17 15:45 | FC Botosani v Shkendija Tetovo | W | 0-1 |
| North Macedonia First League | 2020/09/12 14:00 | Belasica Strumica v Shkendija Tetovo | W | 0-3 |
| North Macedonia First League | 2020/08/31 14:30 | Shkendija Tetovo v FK Borec | D | 1-1 |
| UEFA Europa League Qualifying | 2020/08/27 16:00 | FK Sumqayit v Shkendija Tetovo | W | 0-2 |
| North Macedonia First League | 2020/08/22 15:00 | Makedonija Gj. P v Shkendija Tetovo | W | 0-1 |
| North Macedonia First League | 2020/08/16 15:00 | Shkendija Tetovo v FC Struga Trim & Lum | W | 2-0 |
| North Macedonia First League | 2020/08/09 15:30 | KF Shkupi Skopje v Shkendija Tetovo | D | 2-2 |
Away History
| England Premier League | 2020/09/20 11:00 | Southampton v Tottenham | W | 2-5 |
| UEFA Europa League Qualifying | 2020/09/17 16:00 | Lokomotiv Plovdiv v Tottenham | W | 1-2 |
| England Premier League | 2020/09/13 15:30 | Tottenham v Everton | L | 0-1 |
| Europe Friendlies | 2020/09/05 14:00 | Watford v Tottenham | L | 2-1 |
| Elite Club Friendlies | 2020/08/29 14:00 | Tottenham v Birmingham | W | 1-0 |
| Elite Club Friendlies | 2020/08/28 14:30 | Tottenham v Reading | W | 4-1 |
| Elite Club Friendlies | 2020/08/22 14:00 | Tottenham v Ipswich | W | 3-0 |
| England Premier League | 2020/07/26 15:00 | Crystal Palace v Tottenham | D | 1-1 |