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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.
| Tournament details | |
|---|---|
| Country |  Macedonia |
| Dates | 17 September 2008 – 24 May 2009 |
| Teams | 32 |
| Defending champions | Rabotnichki |
| Final positions | |
| Champions | Rabotnichki (2nd title) |
| Runner-up | Makedonija G.P. |
| Tournament statistics | |
| Matches played | 41 |
| Goals scored | 100 (2.44 per match) |
| 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 |
The draw was held on 21 June 2008 in Skopje. Matches were played on 17 September 2008.
| Team 1 | Score | Team 2 |
|---|---|---|
| 17 September 2008 | ||
| Fortuna (3) | 2–3 | Pobeda (1) |
| Ohrid 2004 (2) | 3–0 (w/o) | Bashkimi (1) |
| Bregalnica Shtip (2) | 0–3 (w/o) | Horizont Turnovo (1) |
| Vardino (3) | 0–4 | Milano (1) |
| Karaorman (3) | 0–3 (w/o) | Belasica (2) |
| Gostivar (3) | 0–3 (w/o) | Miravci (2) |
| Teteks (2) | 0–1 | Makedonija G.P. (1) |
| Lokomotiva (2) | 0–2 | Rabotnichki (1) |
| Nov Milenium (2) | 1–0 | Cementarnica (2) |
| Kravari (3) | 0–4 | Shkëndija 79 (2) |
| Babuna (2) | 0–3 | Vardar (1) |
| Sloga Jugomagnat (1) | 2–4 | Renova (1) |
| 11 Oktomvri (3) | 0–1 | Metalurg (1) |
| Vëllazërimi (2) | 0–2 | Sileks (1) |
| Kozhuf (2) | 1–4 | Pelister (1) |
| Drita (2) | 2–1 | Napredok (1) |
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.
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Metalurg (1) | 0–1 | Milano (1) | 0–1 | 0–0 |
| Vardar (1) | 1–3 | Renova (1) | 1–1 | 0–2 |
| Rabotnichki (1) | 3–0 | Nov Milenium (2) | 1–0 | 2–0 |
| Drita (2) | 1–5 | Miravci (2) | 1–1 | 0–4 |
| Sileks (1) | 2–0 | Belasica (2) | 2–0 | 0–0 |
| Pelister (1) | 6–1 | Horizont Turnovo (1) | 4–0 | 2–1 |
| Pobeda (1) | 1–5 | Makedonija G.P. (1) | 1–1 | 0–4 |
| Shkëndija 79 (2) | 5–1 | Ohrid 2004 (2) | 3–0 | 2–1 |
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 7 and 10 December 2008.
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Renova (1) | 0–1 | Rabotnichki (1) | 0–0 | 0–1 |
| Sileks (1) | 1–4 | Milano (1) | 0–2 | 1–2 |
| Pelister (1) | 3–4 | Shkëndija 79 (2) | 3–1 | 0–3 |
| Miravci (2) | 1–4 | Makedonija G.P. (1) | 1–1 | 0–3 |
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
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Rabotnichki (1) | 3–2 | Shkëndija 79 (2) | 3–1 | 0–1 |
| Makedonija G.P. (1) | 2–1 | Milano (1) | 2–0 | 0–1 |
Matches
| Rabotnichki (1) | 3−1 | Shkëndija 79 (2) |
|---|---|---|
|
| Shkëndija 79 (2) | 1−0 | Rabotnichki (1) |
|---|---|---|
|
Rabotnichki won 3–2 on aggregate.
| Makedonija G.P. (1) | 2−0 | Milano (1) |
|---|---|---|
|
| Milano (1) | 1−0 | Makedonija G.P. (1) |
|---|---|---|
|
Makedonija G.P. won 2–1 on aggregate.
| Rabotnichki (1) | 1–1 (a.e.t.) | Makedonija G.P. (1) |
|---|---|---|
|
Report |
|
| Penalties | ||
| 6–5 |
|
|
- 2008–09 Macedonian Football Cup at FFM.mk
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