2018–19 Macedonian Football Cup

The 2018–19 Macedonian Football Cup was the 27th season of North Macedonia's football knockout competition. Shkëndija were the defending champions, having won their second title in the previous year.

First round
The matches were played on 22 August 2018.


 * colspan="3" style="background-color:#97DEFF" align=center|22 August 2018


 * colspan="3" style="background-color:#97DEFF" align=center|29 August 2018
 * colspan="3" style="background-color:#97DEFF" align=center|29 August 2018


 * colspan="3" style="background-color:#97DEFF" align=center|5 September 2018
 * colspan="3" style="background-color:#97DEFF" align=center|5 September 2018


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Second round
The first legs were played on 19 September and the second legs will be played on 3 October 2018.


 * colspan="2" rowspan="1" N/A
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Quarter-finals
The first legs were played on 7 November and the second legs will be played on 5 December 2018.


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Semi-finals
The first legs were played on 27 February and the second legs on 10 April 2019.

Summary

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Matches
Makedonija G.P. won 2–0 on aggregate.

Akademija Pandev won 6–2 on aggregate.