The 2008–09 Macedonian Football Cup was the 17th season of Macedonia's football knockout competition.
The draw was held on 21 June 2008 in Skopje.
The draw was held on 22 September 2008 in Skopje.
The draw was held on 6 November 2008 in Skopje.
The draw was held on 25 December 2008 in Skopje.