2008–09 Cypriot Cup First round First round

| Team_1 | Agg_ | Team_2 | _1st_leg | _2nd_leg |
|---|---|---|---|---|
| Olympiakos Nicosia | 2–6 | AEL Limassol | 0–3 | 2–3 |
| Nea Salamis | 2–4 | Doxa Katokopias | 1–3 | 1–1 |
| Aris Limassol | 1–2 | AE Paphos | 1–1 | 0–1 |
| Omonia Aradippou | 2–3 | APOP Kinyras | 0–2 | 2–1 |
| AO Ayia Napa | 2–5 | Ethnikos Achna | 2–2 | 0–3 |
| PAEEK | 1–5 | Atromitos Yeroskipou | 0–2 | 1–3 |
| Ethnikos Assia | 2–0 | ASIL Lysi | 0–0 | 2–0 |
| Onisilos Sotira | 1–2 | THOI Lakatamia | 0–1 | 1–1 |
| MEAP Nisou | 0–4 | AEK Larnaca | 0–1 | 0–3 |
| Digenis Morphou | 6–4 | Alki Larnaca | 4–3 | 2–1 |
| Chalkanoras Idaliou | 2–3 | Enosis Neon Paralimni | 2–3 | 0–0 |
| Ermis Aradippou | 3–3 ( a ) | APEP | 1–1 | 2–2 ( aet ) |