Round of 32

16.08.2016 at 17.00 CET:

Sateska (3) – Metalurg (2) 0:3

17.08.2016 at 17.00 CET:

Chaklani (4) – Rabotnichki (1) 1:6
Vlaznimi (3) – Teteks (2) 0:1
Fortuna (3) – Pobeda (1) 0:3 awarded
Belasica (3) – Pelister (1) 2:2 (1:3 p.s.o.)
Akademija Pandev (2) – Makedonija GjP (1) 5:0
Ljuboten (4) – Horizont Turnovo (2) 0:6
Vardar Negotino (2) – Shkupi (1) 0:2
Gorno Lisiche (2) – Renova (1) 1:3
Novaci (2) – Skopje (2) 2:1
Malesh (3) – Sileks (1) 0:1
Kozhuf Miravci (3) – Vlazrimi 77 (2) 0:3 awarded

24.08.2016 at 16:30 CET

Skenderbeu (3) – Vardar (1) 0:9

31.08.2016 at 16:30 CET

Golemo Konjari (3) – Shkendija (1) 0:11

Mladost (4) and Bregalnica (1) had no opponent and automatically advanced to the next round.

Round of 16

first leg: 21.09.2016 at 15.30 CET
return: 12.10.2016 at 14.30 CET

Akademija Pandev (2) – Shkupi (1) 0:1, 1:3 (1:4 agg.)
Sileks (1) – Horizont Turnovo (2) 2:1, 3:3 (5:4 agg.)
Bregalnica (1) – Teteks (2) 4:0, 2:1 (6:1 agg.)
Novaci (2) – Pobeda (1) 1:2, 0:5 (1:7 agg.)

return legs played on 19.10.2016 at 14.30 CET:

Pelister (1) – Renova (1) 2:0, 1:3 (3:3 agg.) (Pelister wins on away goal rule)
Vlazrimi 77 (2) – Vardar (1) 1:3, 0:2 (1:5 agg.)
Rabotnichki (1) – Shkendija (1) 0:2, 0:0 (0:2 agg.)

Metalurg (2) had no opponent and automatically advanced to the next round.

Quarter-finals

first leg: 23.11.2016 at 13.30 CET
return: 07.12.2016 at 13.00 CET

Pelister (1) – Sileks (1) 1:0, 2:1 (3:1 agg.)
Metalurg (2) – Vardar (1) 1:4, 1:4 (2:8 agg.)
Shkupi (1) – Shkendija (1) 0:0, 0:4 (0:4 agg.)
Pobeda (1) – Bregalnica (1) 2:2, 0:3 (2:5 agg.)

Semi-finals

first leg: 01.03.2017
return: 19.04.2017

Vardar (1) – Shkendija (1) 1:3; 1:0 (2:3 agg.)
Bregalnica (1) – Pelister (1) 2:2; 0:1 (2:3 agg.)

Final

17.05.2017 at 17.00 CET at the “Mladost” stadium in Strumica

Shkendija (1) – Pelister (1) 0:0 aet (3:4 p.s.o.) (match report)