The 1998–99 Macedonian Football Cup was the 7th season of Macedonia's football knockout competition.
Vardar defended their title, having won their fourth title.
Pobeda and Vardar were advanced to the quarterfinal, the other teams in group were Kumanovo and Sasa.
Sileks and Osogovo were advanced to the quarterfinal, the other teams in group were Pelister and Ilinden Skopje.
Sources:[1][2][3] The first legs were played on 10 March and second were played on 17 March 1999.