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The 2016–17 Macedonian Football Cup was the 25th season of Macedonia's football knockout competition.[1] Shkëndija are the defending champions, having won their first title in the previous year.
| Round | Date(s) | Fixtures | Clubs | New entries |
|---|---|---|---|---|
| First Round | 16, 17, 24, 31 August 2016[2] | 14 | 30 → 14 | 30 |
| Second Round | 21 September & 12, 19 October 2016 | 14 | 14 → 8 | 2 |
| Quarter-finals | 23 November & 7 December 2016 | 8 | 8 → 4 | none |
| Semi-finals | 1 March & 19 April 2017 | 4 | 4 → 2 | none |
| Final | 17 May 2017 | 1 | 2 → 1 | none |
The matches were played on 16, 17, 24, and 31 August 2016.[2]
| Team 1 | Score | Team 2 |
|---|---|---|
| 16 August 2016 | ||
| Sateska (3) | 0–3 | Metalurg (2) |
| 17 August 2016 | ||
| Çakllani (4) | 1–6 | Rabotnichki (1) |
| Vlaznimi (3) | 0–1 | Teteks (2) |
| Fortuna (3) | 0–3 | Pobeda (1) |
| Belasica (3) | 2–2 (1–3 p) | Pelister (1) |
| Akademija Pandev (2) | 5–0 | Makedonija G.P. (1) |
| Ljuboten (4) | 0–6 | Horizont Turnovo (2) |
| Vardar Negotino (2) | 0–2 | Shkupi (1) |
| Gorno Lisiche (2) | 1–3 | Renova (1) |
| Novaci (2) | 2–1 | Skopje (2) |
| Malesh (3) | 0–1 | Sileks (1) |
| Kozhuf (3) | 0–3 | Vëllazërimi 77 (2) |
| 24 August 2016 | ||
| Skënderbeu Poroj (3) | 0–9 | Vardar (1) |
| 31 August 2016 | ||
| Golemo Konjari (3) | 0–11 | Shkëndija (1) |
| N/A | ||
| Bregalnica Shtip (1) | bye | |
| Mladost Carev Dvor (x) | bye | |
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Entering this round are the 14 winners from the First Round and Bregalnica Shtip who got a bye to this round. Mladost Carev Dvor withdrew from the competition, so their opponents Metalurg got a bye to the next round. The draw was held on 2 September 2016. The first legs were played on 21 September and the second legs were played on 12 and 19 October 2016.
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Akademija Pandev (2) | 1–4 | Shkupi (1) | 0–1 | 1–3 |
| Pelister (1) | (a) 3–3 | Renova (1) | 2–0 | 1–3 |
| Vëllazërimi 77 (2) | 1–5 | Vardar (1) | 1–3 | 0–2 |
| Sileks (1) | 5–4 | Horizont Turnovo (2) | 2–1 | 3–3 |
| Bregalnica Shtip (1) | 6–1 | Teteks (2) | 4–0 | 2–1 |
| Novaci (2) | 1–7 | Pobeda (1) | 1–2 | 0–5 |
| Rabotnichki (1) | 0–2 | Shkëndija (1) | 0–2 | 0–0 |
| Metalurg (2) | w/o | Mladost Carev Dvor (x) | – | – |
| Bregalnica Shtip (1) | bye | |||
The first legs were played on 23 November 2016 and the second legs played on 7 December 2016.
The first legs were played on 1 March 2017 and the return legs played on 19 April 2017.
Summary
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Vardar (1) | 2–3 | Shkëndija (1) | 1–3 | 1–0 |
| Bregalnica Shtip (1) | 2–3 | Pelister (1) | 2–2 | 0–1 |
Matches
Shkëndija won 3–2 on aggregate.
| Bregalnica Shtip (1) | 2–2 | Pelister (1) |
|---|---|---|
|
Report |
| Pelister (1) | 1–0 | Bregalnica Shtip (1) |
|---|---|---|
|
Report |
Pelister won 3–2 on aggregate.
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Top scorers
- As of 17 May 2016.
| Rank | Player | Club | Goals |
|---|---|---|---|
| 1 |  Besart Ibraimi |
Shkendija | 5 |
| 2 | Goran Zdravkov |
Bregalnica | 4 |
| Petar Petkovski |
Vardar | ||
| Mario Krstovski |
Horizont Turnovo | ||
| 5 |  Juan Felipe |
Vardar | 3 |
 Jhon Obregón | |||
| Jonathan Balotelli | |||
| Nikola Bozhinov |
Horizont Turnovo | ||
| Dejan Zdraveski |
Pobeda Prilep | ||
| Lazar Ilijev |
Bregalnica | ||
| Demir Imeri |
Shkendija | ||
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