Round of 32

21.08.2013

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Zajazi – Vardar 2:4
Lokomotiva – Napredok 1:5
Babi – Gostivar 0:3 (awarded)
Karaorman – Pelister 0:5
Belasica – Horizont Turnovo 0:4
Rabotnik Djumajlija – Shkendija 0:7
Sateska – Bregalnica 0:3 (awarded)
Karbinci – Rabotnichki 1:9
11 Oktomvri – Renova 0:4
Mogila – Sileks 2:3
Novaci – Gorno Lisiche 2:1
Shkupi – Teteks 0:3 (awarded)
Korzo – Metalurg 0:1
Miravci – Rufeja 3:0
Borec – Drita 1:2
Ljuboten – Makedonija GjP 0:3

Round of 16

first leg: 18.09.2013
return: 25.09.2013

Metalurg – Vardar 1:0, 1:2 (2:2 agg.) (Metalurg wins on away goal rule)
Horizont Turnovo – Bregalnica 1:0, 0:1 (1:1 agg.) 0:3 p.s.o.
Teteks – Renova 2:2, 2:2 (4:4 agg.) 5:4 p.s.o.
Pelister – Miravci 2:0, 0:2 (2:2 agg.), 3:2 p.s.o.
Rabotnichki – Novaci 4:0, 2:1 (6:1 agg.)
Sileks – Drita 1:0, 0:1 (1:1 agg.) 7:8 p.s.o.
Gostivar – Napredok 0:3, 2:1 (2:4 agg.)
Shkendija – Makedonija Gjorche Petrov 2:0, 2:0 (4:0 agg.)

Quarter-finals

first leg: 12.10.2014
return: 20.11.2014

Teteks – Napredok 0:0. 2:1 (2:1 agg.)
Bregalnica – Shkendija 2:1, 1:1 (3:2 agg.)
Drita – Metalurg 0:3, 1:7 (1:10 agg.)
Pelister – Rabotnichki 1:0, 0:2 (1:2 agg.)

Semi-finals

first leg: 19.03.2014
return: 16.05.2014

Rabotnichki – Bregalnica 2:0, 0:2 (2:2 agg.) 5:4 p.s.o.
Teteks – Metalurg 0:0, 0:1 (0:1 agg.)

Final

07.05.2014 at the “National Arena Philip II of Macedon” in Skopje
Rabotnichki – Metalurg 2:0