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| 20.08.2023 | 17:00 | FK Bregalnica Štip | - | KF Gostivari | 2:1 (1:0) | |
| 17:00 | FK Rabotnički | - | Makedonija GP | 1:0 (1:0) | ||
| 17:00 | KF Shkupi | - | Sileks Kratovo | 1:1 (1:0) | ||
| 17:00 | GFK Tikvesh | - | KF Shkëndija 79 | 1:2 (1:2) | ||
| 17:00 | FK Voska Sport | - | Vardar Skopje | 3:2 (2:0) | ||
| 21.08.2023 | 17:00 | FC Struga | - | FK AP Brera Strumica | 1:2 (0:1) |
| » Classement | équipe recevante | à l'extérieur | Premier tour | Second tour |
| # | Équipe | M. | G. | N. | P. | Buts | Diff. | Pts. | |
|---|---|---|---|---|---|---|---|---|---|
| 1 |
|
KF Shkëndija 79 | 3 | 3 | 0 | 0 | 4:1 | 3 | 9 |
| 2 |
|
FK AP Brera Strumica | 3 | 3 | 0 | 0 | 5:1 | 4 | 9 |
| 3 |
|
GFK Tikvesh | 3 | 2 | 0 | 1 | 5:2 | 3 | 6 |
| 4 |
|
FK Bregalnica Štip | 3 | 2 | 0 | 1 | 4:3 | 1 | 6 |
| 5 |
|
FK Rabotnički | 3 | 2 | 0 | 1 | 4:3 | 1 | 6 |
| 6 |
|
Sileks Kratovo | 3 | 1 | 1 | 1 | 4:3 | 1 | 4 |
| 7 |
|
KF Shkupi | 3 | 1 | 1 | 1 | 3:4 | -1 | 4 |
| 8 |
|
Makedonija GP | 3 | 1 | 0 | 2 | 1:2 | -1 | 3 |
| 9 |
|
FC Struga | 3 | 1 | 0 | 2 | 3:3 | 0 | 3 |
| 10 |
|
FK Voska Sport | 3 | 1 | 0 | 2 | 3:5 | -2 | 3 |
| 11 |
|
Vardar Skopje | 3 | 0 | 0 | 3 | 2:5 | -3 | 0 |
| 12 |
|
KF Gostivari | 3 | 0 | 0 | 3 | 1:7 | -6 | 0 |
| Champions League Quali. | |
| Relégation | |
| Relégation |
