Pobeda Prilep

Ground: "Filip II Arena"-Skopje
Referee: Zoran Boshkov (Negotino)
Yellow cards: Vandair (R) Nestoroski, Churlinov (P)
Man of the match: Dushan Savik

• [24] Savik (R)
  
• [28] B. Bozhinovski (R)
• [29] Petrović (P)
• [38] Savik (R)
  
• [43] Vandair (R)
  
• [55] Nestoroski (P)
• [73] Savik (R)
  
• [86] B. Bozhinovski (R)
  

Rabotnicki: Naumovski, Dimovski, Ristov, Muarem, V.Bozhinovski, Ze Karlos (R.Karlos), Savik, Gligorov (Todoroski), Vandair (Petkovski), B.Bozinovski, Fernando
Pobeda: Pashovski, Mitrevski (Gjorgjioski), Damevski (Spirkoski), Petrović, Mircheski, Meglenski, Jovanović, Marković, Aceski (Stojanov), Nestoroski, Churlinov

Rabotnicki 6 - 2 Pobeda (24.10.2009)

Ground: City Stadium "Goce Delcev" Prilep
Referee: Aleksandar Angelov (Kochani)
Yellow cards: Emini, Maliki (M)
Man of the match: Cvetan Churlinov

• [1] Churlinov (P)
  
• [10] Nestoroski (P)
• [26] Churlinov (P)
• [40] Mircheski (P)
• [60] A.Sulejmani (M)
  

Pobeda: Pashovski (Jeftimov), Mitrevski, Damevski (Koteski), Mircheski, Stojanov, Meglenski, Aceski, Ristov, Markovik, Nestoroski, Churlinov (Dunimagloski)
Milano: Abduli, Abazi (Emini), F.Maliki, Shabani, Aliju, Memeti, F.Sulejmani (Anifovik), Limani, Jasharevik (D.Maliki), Beljuli, A.Sulejmani

Pobeda 4 - 1 Milano (18.10.2009)

Ground: "Zelezarnica"-Avtokomanda, Skopje
Referee: Zoran Petkovski (Veles)
Yellow cards: Tadić, Stefanović, Ilijoski, Ruteski (M) Stojanov (P)
Man of the match: Krste Velkovski

• [10] Stefanović (M)
  
• [65] Marković (P)
• [76] Velkovski (M)

Metalurg: Manchevski, Tadić (Ilijoski), Lazarevski, Dimitrovski, Cvetanovski, Trajchev, Krstev, Neno, Gjurić (Ruteski), Stefanović (Geshoski), Velkovski
Pobeda: Pashovski, Stojanov, Jovanović (Aceski), Dameski, Mitrevski, Mircheski, Meglenski, Ristov (Churlinov), Petrović, Marković, Nestoroski

Metalurg 2 - 1 Pobeda (04.10.2009)