The 2008–09 Macedonian Football Cup was the 17th season of Macedonia's football knockout competition. Rabotnichki defended their title, having won their second title.
Competition calendar Round Date(s) Fixtures Clubs New entries First Round 17 September 2008 16 32 → 16 32 Second Round 22, 29, 30 October 2008 16 16 → 8 none Quarter-finals 26 November & 7, 10 December 2008 8 8 → 4 none Semi-finals 8 April & 6 May 2009 4 4 → 2 none Final 24 May 2009 1 2 → 1 none
First round The draw was held on 21 June 2008 in Skopje. Matches were played on 17 September 2008.
|colspan="3" style="background-color:#97DEFF" align=center|17 September 2008
Second round The draw was held on 22 September 2008 in Skopje. The first legs were played on 22 October 2008 and second on 29 and 30 October 2008.
Quarter-finals The draw was held on 6 November 2008 in Skopje. The first legs were played on 26 November 2008 and the second were played on 6 and 10 December 2008.
Summary
Matches
Rabotnichki won 1–0 on aggregate.
Milano won 4–1 on aggregate.
Shkëndija 79 won 4–3 on aggregate.
Makedonija G.P. won 4–1 on aggregate.
Semi-finals The draw was held on 25 December 2008 in Skopje. The first legs were played on 8 April 2009 and the second were played on 6 May 2009.
Summary
Matches
Rabotnichki won 3–2 on aggregate.
Makedonija G.P. won 2–1 on aggregate.
Final
See also 2008–09 Macedonian First Football League 2008–09 Macedonian Second Football League
References
External links 2008–09 Macedonian Football Cup at FFM.mk