| 2024-03-06 10:00 | R22 | Vardar |  | 1-0 |  | Rabotnicki | Darko Glisic 56' | |
| 2024-03-03 10:00 | R21 | Rabotnicki | | 2-0 |  | FK Bregalnica | Marcelin Gando 45', Sodiq Rasheed 80' | |
| 2024-02-25 10:00 | R20 | Vardar | | 2-0 | | FK Bregalnica | Marjan Altiparmakovski 21' (pen.), Darko Glisic 24' | |
| 2024-02-18 10:00 | R19 | Rabotnicki | | 0-0 |  | FK Struga | | |
| 2023-12-10 09:00 | R18 | Vardar | | 2-0 |  | GFK Tikves | Darko Glisic 23', David Velkovski 83' | |
| 2023-12-03 09:00 | R17 | Rabotnicki | | 1-0 |  | Brera Strumica | Ermedin Adem 70' | |
| 2023-11-29 09:00 | R16 | Vardar | | 1-3 | | FK Struga | Mihajlo Milosavic 32' (pen.); Vangjel Zguro 7' (pen.), Hadis Tairi 12', Bassirou Compaoré 62' | |
| 2023-11-26 09:00 | R15 | Rabotnicki | | 0-0 |  | KF Gostivari | | |
| 2023-11-11 09:00 | R14 | Vardar | | 1-2 |  | Voska Sport | Alen Jasaroski 4' 75', Fatih Ismaili 15' (g.c.) | |
| 2023-11-04 09:00 | R13 | Rabotnicki | | 1-0 |  | Sileks FC | Stefan Despotovski 54' | |
| 2023-10-29 09:00 | R12 | Vardar | | 1-0 | | Brera Strumica | Azer Omeragikj 7' | |
| 2023-10-22 09:00 | R11 | Rabotnicki | | 0-1 | | Vardar | Darko Micevski 77' (pen.) | |
| 2023-10-08 09:00 | R10 | Vardar | | 0-2 |  | KF Shkendija 79 | Metodi Maksimov 65', Almir Aganspahic 90' | |
| 2023-10-01 09:00 | R9 | Rabotnicki | | 1-0 | | GFK Tikves | Atdhe Mazari 22' | |
| 2023-09-24 10:00 | R8 | Vardar | | 0-2 | | KF Gostivari | Lanry Kehinde 32', Goba Zakpa 88' | |
| 2023-09-17 10:00 | R7 | Rabotnicki | | 2-0 | | Voska Sport | Krste Velkoski 32' (pen.), Marcelin Gando 59' | |
| 2023-09-02 11:00 | R6 | Vardar | | 2-1 |  | Makedonija GP | Darko Micevski 25' (pen.), Azer Omeragikj 33'; Nikola Velichkovski 90' | |
| 2023-08-27 11:00 | R5 | Rabotnicki | | 1-2 | | KF Shkendija 79 | Shafiq Kagimu 28'; Bruno Dita 90', Endrit Krasniqi 90' | |
| 2023-08-23 11:30 | R4 | Vardar | | 2-2 | | Sileks FC | Darko Micevski 40' (pen.), David Velkovski 60'; Darko Angjeleski 52', Kristijan Eftimov 86' | |
| 2023-08-20 12:00 | R3 | Rabotnicki | | 1-0 | | Makedonija GP | Krste Velkoski 21' | |
| 2023-08-13 12:00 | R2 | Vardar | | 0-1 |  | Shkupi 1927 | Niltinho 79' | |
| 2023-08-10 12:00 | 3E | FK Struga | | 3-1 |  | Swift Hesperange | Besart Ibraimi 22' 40' (pen.) 77' (pen.); Dominik Stolz 46' | |
| 2023-08-07 12:00 | R1 | Rabotnicki | | 3-1 | | Shkupi 1927 | Atdhe Mazari 1', Mevlan Murati 82' (pen.), Georg Stojanovski 90'; Darko Ilieski 62' | |
| 2023-07-27 16:00 | 2E | Shkupi 1927 | | 0-2 |  | Levski Sofia | Welton 30', Ronaldo 90' | |
| 2023-07-13 15:00 | 1PE | KF Shkendija 79 | | 1-0 |  | Haverfordwest County | Adenis Shala 47' | |
01/05 - 10:00
01/05 - 16:00
01/05 - 16:00
01/05 - 16:00
01/05 - 16:30
01/05 - 23:15
