*Bregalnica Stip 3-2 Shkendija'79
| 20.11.2013 | Shkendija'79 | 1-1 | Bregalnica Stip | |
| 12.10.2013 | Bregalnica Stip | 2-1 | Shkendija'79 | |
Drita Bogovinje 1-10 Metalurg Skopje *
| 20.11.2013 | Metalurg Skopje | 7-1 | Drita Bogovinje | |
| 13.10.2013 | Drita Bogovinje | 0-3 | Metalurg Skopje | |
Pelister Bitola 1-2 Rabotnicki Skopje *
| 04.12.2013 | Rabotnicki Skopje | 2-0 | Pelister Bitola | |
| 13.10.2013 | Pelister Bitola | 1-0 | Rabotnicki Skopje | |
*Teteks Tetovo 2-1 Napredok Kicevo
| 20.11.2013 | Napredok Kicevo | 1-2 | Teteks Tetovo | |
| 13.10.2013 | Teteks Tetovo | 0-0 | Napredok Kicevo | |