1999–2000 Macedonian Football Cup

The 1999–2000 Macedonian Football Cup was the 8th season of Macedonia's football knockout competition. Vardar were the defending champions, having won their fourth title. The 1999–2000 champions were Sloga Jugomagnat who won their second title.

Competition calendar
Source:

First round

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Quarter-finals
The first legs were played on 15 March and second were played on 22 March 2000.


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Semi-finals
The first legs were played on 5 April and the second were played on 19 and 20 April 2000.

Summary

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Matches
Pobeda won 4–3 on aggregate.

Sloga Jugomagnat won 4–2 on aggregate.