| 2024-03-06 14:00 | G22 | Vardar |  | 1-0 |  | Rabotnicki | Darko Glisic 56' | |
| 2024-03-03 14:00 | G21 | Rabotnicki | | 2-0 |  | FK Bregalnica | Marcelin Gando 45', Sodiq Rasheed 80' | |
| 2024-02-25 14:00 | G20 | Vardar | | 2-0 | | FK Bregalnica | Marjan Altiparmakovski 21' (r), Darko Glisic 24' | |
| 2024-02-18 14:00 | G19 | Rabotnicki | | 0-0 |  | FK Struga | | |
| 2023-12-10 13:00 | G18 | Vardar | | 2-0 |  | GFK Tikves | Darko Glisic 23', David Velkovski 83' | |
| 2023-12-03 13:00 | G17 | Rabotnicki | | 1-0 |  | Brera Strumica | Ermedin Adem 70' | |
| 2023-11-29 13:00 | G16 | Vardar | | 1-3 | | FK Struga | Mihajlo Milosavic 32' (r); Vangjel Zguro 7' (r), Hadis Tairi 12', Bassirou Compaoré 62' | |
| 2023-11-26 13:00 | G15 | Rabotnicki | | 0-0 |  | KF Gostivari | | |
| 2023-11-11 13:00 | G14 | Vardar | | 1-2 |  | Voska Sport | Alen Jasaroski 4' 75', Fatih Ismaili 15' (a.g.) | |
| 2023-11-04 13:00 | G13 | Rabotnicki | | 1-0 |  | Sileks FC | Stefan Despotovski 54' | |
| 2023-10-29 13:00 | G12 | Vardar | | 1-0 | | Brera Strumica | Azer Omeragikj 7' | |
| 2023-10-22 14:00 | G11 | Rabotnicki | | 0-1 | | Vardar | Darko Micevski 77' (r) | |
| 2023-10-08 14:00 | G10 | Vardar | | 0-2 |  | KF Shkendija 79 | Metodi Maksimov 65', Almir Aganspahic 90' | |
| 2023-10-01 14:00 | G9 | Rabotnicki | | 1-0 | | GFK Tikves | Atdhe Mazari 22' | |
| 2023-09-24 15:00 | G8 | Vardar | | 0-2 | | KF Gostivari | Lanry Kehinde 32', Goba Zakpa 88' | |
| 2023-09-17 15:00 | G7 | Rabotnicki | | 2-0 | | Voska Sport | Krste Velkoski 32' (r), Marcelin Gando 59' | |
| 2023-09-02 16:00 | G6 | Vardar | | 2-1 |  | Makedonija GP | Darko Micevski 25' (r), Azer Omeragikj 33'; Nikola Velichkovski 90' | |
| 2023-08-27 16:00 | G5 | Rabotnicki | | 1-2 | | KF Shkendija 79 | Shafiq Kagimu 28'; Bruno Dita 90', Endrit Krasniqi 90' | |
| 2023-08-23 16:30 | G4 | Vardar | | 2-2 | | Sileks FC | Darko Micevski 40' (r), David Velkovski 60'; Darko Angjeleski 52', Kristijan Eftimov 86' | |
| 2023-08-20 17:00 | G3 | Rabotnicki | | 1-0 | | Makedonija GP | Krste Velkoski 21' | |
| 2023-08-13 17:00 | G2 | Vardar | | 0-1 |  | Shkupi 1927 | Niltinho 79' | |
| 2023-08-10 17:00 | 3E | FK Struga | | 3-1 |  | Swift Hesperange | Besart Ibraimi 22' 40' (r) 77' (r); Dominik Stolz 46' | |
| 2023-08-07 17:00 | G1 | Rabotnicki | | 3-1 | | Shkupi 1927 | Atdhe Mazari 1', Mevlan Murati 82' (r), Georg Stojanovski 90'; Darko Ilieski 62' | |
| 2023-07-27 21:00 | 2TP | Shkupi 1927 | | 0-2 |  | Levski Sofia | Welton 30', Ronaldo 90' | |
| 2023-07-13 20:00 | 1TP | KF Shkendija 79 | | 1-0 |  | Haverfordwest County | Adenis Shala 47' | |
