2008–09 Macedonian Football Cup
 | This article documents a current sporting event. Information may change rapidly as the event progresses. Initial news reports, scores, or statistics may be unreliable. The last updates to this article may not reflect the most current information. |
The 2008-09 Macedonian Cup is the 17th edition of Macedonia's football knockout competition. FK Rabotnički are the defending champions, having won their first title.
First round
The draw was held on June 21 2008 in Skopje. Matches were played on September 17 2008.
| Team 1 | Score | Team 2 |
|---|---|---|
| Fortuna | 2–3 | Pobeda |
| Ohrid 2004 | 3–0 (f) | Baškimi |
| Bregalnica Štip | (f) 0–3 | Horizont Turnovo |
| Vardino | 0–4 | Milano |
| Karaorman | (f) 0–3 | Belasica |
| Gostivar | (f) 0–3 | Miravci |
| Teteks | 0–1 | Makedonija |
| Lokomotiva | 0–2 | Rabotnički |
| Nov Milenium | 1–0 | Cementarnica |
| Kravari | 0–4 | Škendija 79 |
| Babuna | 0–3 | Vardar |
| Sloga Jugomagnat | 2–4 | Renova |
| 11 Oktomvri | 0–1 | Metalurg |
| Vlazrimi | 0–2 | Sileks |
| Kožuv | 1–4 | Pelister |
| Drita | 2–1 | Napredok |
Second round
The draw was held on September 22 2008 in Skopje. The first legs were played on October 22 2008 and second on October 29 and 30, 2008.
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Metalurg | 0–1 | Milano | 0–1 | 0–0 |
| Vardar | 1–3 | Renova | 1–1 | 0–2 |
| Rabotnički | 3–0 | Nov Milenium | 1–0 | 2–0 |
| Drita | 1–5 | Miravci | 1–1 | 0–4 |
| Sileks | 2–0 | Belasica | 2–0 | 0–0 |
| Pelister | 6–1 | Horizont Turnovo | 4–0 | 2–1 |
| Pobeda | 1–5 | Makedonija | 1–1 | 0–4 |
| Škendija 79 | 5–1 | Ohrid 2004 | 3–0 | 2–1 |
Quarterfinals
The draw will be held on November 6 2008 in Skopje.
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| – | – | – | ||
| – | – | – | ||
| – | – | – | ||
| – | – | – |
Semifinals
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| – | – | – | ||
| – | – | – |
Final
| Winners of semifinal 1 | – | Winners of semifinal 2 |
|---|---|---|