| 2. Runde | 26.07.2023 | FC Struga | - | FK Budućnost Podgorica | 1:0 |  |
 |
||
| 2. Runde | 01.08.2023 | FK Budućnost Podgorica | - | FC Struga | 3:4 | |
|||
| 3. Runde | 10.08.2023 | FC Struga | - | Swift Hesperange | 3:1 | |
|||
| 3. Runde | 17.08.2023 | Swift Hesperange | - | FC Struga | 2:1 | |
|||
| Playoffs | 24.08.2023 | FC Struga | - | Breiðablik | 0:1 | ||||
| Playoffs | 31.08.2023 | Breiðablik | - | FC Struga | 1:0 |
Nordmazedonien