Sileks Kratovo 1-1 Drita Bogovinje *
| 25.09.2013 | Drita Bogovinje | 1-0/p.8-7 | Sileks Kratovo | |
| 18.09.2013 | Sileks Kratovo | 1-0 | Drita Bogovinje | |
FK Turnovo 1-1 Bregalnica Stip *
| 25.09.2013 | Bregalnica Stip | 1-0/p.3-0 | FK Turnovo | |
| 18.09.2013 | FK Turnovo | 1-0 | Bregalnica Stip | |
*Shkendija'79 4-0 Makedonija GP
| 25.09.2013 | Makedonija GP | 0-2 | Shkendija'79 | |
| 18.09.2013 | Shkendija'79 | 2-0 | Makedonija GP | |
*Metalurg Skopje 2-2 Vardar Skopje
| 25.09.2013 | Vardar Skopje | 2-1 | Metalurg Skopje | |
| 18.09.2013 | Metalurg Skopje | 1-0 | Vardar Skopje | |
Gostivari 2-4 Napredok Kicevo *
| 25.09.2013 | Napredok Kicevo | 1-2 | Gostivari | |
| 18.09.2013 | Gostivari | 0-3 | Napredok Kicevo | |
*Rabotnicki Skopje 6-1 Novaci
| 25.09.2013 | Novaci | 1-2 | Rabotnicki Skopje | |
| 18.09.2013 | Rabotnicki Skopje | 4-0 | Novaci | |
*Pelister Bitola 2-2 FK Miravci
| 25.09.2013 | FK Miravci | 2-0/p.2-3 | Pelister Bitola | |
| 18.09.2013 | Pelister Bitola | 2-0 | FK Miravci | |
*Teteks Tetovo 4-4 Renova
| 25.09.2013 | Renova | 2-2/p.4-5 | Teteks Tetovo | |
| 18.09.2013 | Teteks Tetovo | 2-2 | Renova | |