2008–09 Cypriot Cup Second round Second round

| Team_1 | Agg_ | Team_2 | _1st_leg | _2nd_leg |
|---|---|---|---|---|
| AEK Larnaca | 1–3 | APOP Kinyras | 0–2 | 1–1 |
| Omonia | 5–2 | Digenis Morphou | 3–1 | 2–1 |
| AE Paphos | 1–3 | AEL Limassol | 0–1 | 1–2 |
| Ermis Aradippou | 7–2 | THOI Lakatamia | 3–1 | 4–1 |
| APOEL | 5–4 | Doxa Katokopias | 2–2 | 3–2 |
| Ethnikos Assia | 2–8 | Ethnikos Achna | 1–5 | 1–3 |
| Atromitos Yeroskipou | 0–3 | Enosis Neon Paralimni | 0–0 | 0–3 |
| Anorthosis | 3–4 | Apollon | 2–1 | 1–3 ( aet ) |