1995/96
Round 1
Sloga Jugomagnat 2-0 Kumanovo
Round 2
First Leg
Sloga Jugomagnat 0-0 Sileks
Second Leg
Sileks 1-1 Sloga Jugomagnat
Quarterfinals
First Leg
Bregalnica Shtip 1-1 Sloga Jugomagnat
Second Leg
Sloga Jugomagnat 3-1 Bregalnica Shtip
Semifinals
First Leg
Shkendija Arachinovo 1-2 Sloga Jugomagnat
Second Leg
Sloga Jugomagnat 2-1 Shkendija Arachinovo