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The 1995–96 Macedonian Football Cup was the 4th season of Macedonia's football knockout competition. Vardar were the defending champions, having won their second title. The 1995–96 champions were Sloga Jugomagnat who won their first title.

Competition calendar

Round	Date(s)	Fixtures	Clubs	New entries
First Round	13 August 1995	16	32 → 16	32
Second Round	8 November & 7 December 1995	16	16 → 8	none
Quarter-finals	3, 20 March 1996	8	8 → 4	none
Semi-finals	17 April & 1 May 1996	4	4 → 2	none
Final	23 May 1996	1	2 → 1	none

Source:^[1]

Matches were played on 13 August 1995.

Team 1	Score	Team 2
Vardar (1)	13–0	Pobeda Valandovo (3)
Sloga Jugomagnat (1)	2–0	Kumanovo (2)

Source:^[1]^[2]

The first legs were played on 8 November and second were played on 7 December 1995.

Team 1	Agg.Tooltip Aggregate score	Team 2	1st leg	2nd leg
Vardar (1)	9–3	Balkan (1)	3–1	6–2
Sloga Jugomagnat (1)	(a) 1–1	Sileks (1)	0–0	1–1

Source:^[1]^[2]

The first legs were played on 3 March and second were played on 20 March 1996.

Team 1	Agg.Tooltip Aggregate score	Team 2	1st leg	2nd leg
Makedonija G.P. (2)	1–4	Vardar (1)	0–1	1–3
Ljuboten (1)	?	Shkëndija Arachinovo (2)	?	?
Pelister (1)	?	FCU 55 (1)	?	?
Bregalnica Shtip (1)	2–4	Sloga Jugomagnat (1)	1–1	1–3

Sources:^[1]^[2]

The first legs were played on 17 April and the second were played on 1 May 1996.

Team 1	Agg.Tooltip Aggregate score	Team 2	1st leg	2nd leg
Vardar (1)	4–1	Pelister (1)	3–0	1–1
Shkëndija Arachinovo (2)	2–4	Sloga Jugomagnat (1)	1–2	1–2

Sources:^[1]^[2]

23 May 1996

18:30 CEST

Vardar (1)	0–0 (a.e.t.)	Sloga Jugomagnat (1)
	Report
Penalties
Markovski Karadjov Trajchov Nikolovski	3–5	Beqiri Demjanski Tuna Tasev Memedi

Attendance: 18,000

Referee: Gjoko Stojanovski (Skopje)

^ ^a ^b ^c ^d ^e ^f "FK Vardar (MKD) results from 1992 to 2000". Google Groups. 17 May 2024. Retrieved 17 May 2024.
^ ^a ^b ^c ^d "Macedonian Cup results from 1993 to 1999". Google Groups. 17 May 2024. Retrieved 17 May 2024.