2008–09 Macedonian Cup Second round Second round

| 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 |