First round
edit| 28 October 2020 | AO Paxoi (5) | 0–8 | Acheron Kanalaki FC (4) |
| 28 October 2020 | АЕ Agiou Leonta Koiliomenou (5) | 0–3 | Pallixouriakos FC (4) |
| 28 October 2020 | AO Mesotopos (5) | 0–2 | Agios Ierotheos FC (4) |
| 28 October 2020 | Orfeas Puma Xanthis (4) | 1–0 | AE Ampelokipon Dramas (4) |
| 28 October 2020 | Ktinotrofikos Asteras Kalirachis (4) | 1–0 | Eordaikos 2007 (5) |
| 28 October 2020 | Anagennisi Artas (4) | 4–1 | Potamia FC (5) |
| 28 October 2020 | Panthiraikos FC (4) | 3–0 | PAO Kokkinou (5) |
| 28 October 2020 | AS Ellispontos Neas Lampsakou (5) | 0–1 | AO Hephaestus Vrontama (5) |
| 28 October 2020 | Keratsini (4) | 2–2 (a.e.t.) (5–4 p) | GFS Aris Archangelou 1947 (5) |
| 28 October 2020 | AO Talos Melidoniou (5) | 0–8 | AO Kyanos Asteras Varis (4) |
| 28 October 2020 | AE Didymoteicho (4) | 2–3 | AS Nestos Chrisoupolis (4) |
| 28 October 2020 | Megas Alexandros Kallithea (4) | 1–0 | Falaniakos AO Falanis (5) |
| 28 October 2020 | AE Karitsa (4) | 2–0 | AS Ethnikos Giannitson (4) |
| 28 October 2020 | AO Megalon Kalyvion (5) | 1–2 | Atromitos Palamas (4) |
| 28 October 2020 | Missolonghi FC (4) | 2–0 | Atromitos Patras FC (5) |
| 28 October 2020 | Pamvouprasiakos AO Varda FC (4) | 0–1 | AO Diavolitsi (4) |
| 28 October 2020 | Iraklis Xylokastrou 1928 (5) | 0–0 (a.e.t.) (4–3 p) | AO Koronida Koiladas (4) |
| 28 October 2020 | Agios Nikolaos (4) | 1–1 (a.e.t.) (5–4 p) | Minotavros (5) |
| 28 October 2020 | Panthrakikos (5) | 1–0 | Anatoli Serron (5) |
Second round
edit| 4 November 2020 | Atromitos Palamas (4) | 2–0 | AO Kyanos Asteras Varis (4) |
| 4 November 2020 | Acheron Kanalaki FC (4) | 0–1 (a.e.t.) | Missolonghi FC (4) |
| 4 November 2020 | AO Hephaestus Vrontama (5) | 0–2 | Iraklis Xylokastrou 1928 (5) |
| 4 November 2020 | Agios Ierotheos FC (4) | 1–0 | Panthiraikos FC (4) |
| 4 November 2020 | AO Diavolitsi (4) | 2–1 | Pallixouriakos FC (4) |
| 5 November 2020 | Megas Alexandros Kallithea (4) | 1–0 | AS Nestos Chrisoupolis (4) |
| 5 November 2020 | Ktinotrofikos Asteras Kalirachis (4) | 0–2 | Anagennisi Artas (4) |
| 5 November 2020 | Orfeas Puma Xanthis (4) | 2–0 | Panthrakikos (5) |
| 5 November 2020 | Agios Nikolaos (4) | 0–1 | Keratsini (4) |
Third round
edit| 2021 | AE Karitsa (4) | 0–2 | Kallithea (3) |
| 2021 | Triglia (3) | 1–2 | Megas Alexandros Kallithea (4) |
| 2021 | Thesprotos (3) | 1–0 (a.e.t.) | Olympiacos Volos (4) |
| 2021 | Missolonghi FC (4) | 0–1 | AEP Kozani (3) |
| 2021 | Kavala (3) | 0–0 (a.e.t.) (3–4 p) | Niki Volos (3) |
| 2021 | Egaleo (3) | 0–0 (a.e.t.) (2–4 p) | Atromitos Palamas (4) |
| 2021 | Pierikos (3) | 1–2 | AO Diavolitsi (4) |
| 2021 | Aspropyrgos (3) | 1–0 | Almopos Aridea (3) |
| 2021 | Kalamata (3) | 1–0 | Santorini 2020 (3) |
| 2021 | Asteras Vlachioti (3) | 2–0 (a.e.t.) | Iraklis Xylokastrou 1928 (5) |
| 2021 | Anagennisi Artas (4) | 0–0 (a.e.t.) (4–5 p) | Keratsini (4) |
| 2021 | Panserraikos (3) | 1–2 | Agios Ierotheos FC (4) |
| 2021 | Apollon Pontus (3) | 4–1 | Orfeas Puma Xanthis (4) |
Fourth round
edit| 2021 | Diagoras (2) | 0–1 | Karaiskakis (2) |
| 2021 | Xanthi (2) | 1–0 (a.e.t.) | Atromitos Palamas (4) |
| 2021 | Veria (3) | 3–0 | Agios Ierotheos FC (4) |
| 2021 | AO Diavolitsi (4) | 0–1 | Keratsini (4) |
| 2021 | Megas Alexandros Kallithea (4) | 0–1 | AEP Kozani (3) |
| 2021 | Levadiakos (2) | 1–0 (a.e.t.) | Ialysos (3) |
| 2021 | Aspropyrgos (3) | 1–0 | Trikala (2) |
| 2021 | Niki Volos (3) | 2–0 | Kalamata (3) |
| 2021 | Apollon Pontus (3) | 0–0 (a.e.t.) (2–4 p) | Panachaiki (2) |
| 2021 | Thesprotos (3) | 0–0 (a.e.t.) (5–6 p) | Ergotelis (2) |
| 2021 | O.F. Ierapetra (2) | 0–0 (a.e.t.) (6–5 p) | Chania (2) |
| 2021 | Asteras Vlachioti (3) | 0–1 (a.e.t.) | Doxa Drama (2) |
Fifth round
edit| 2021 | Apollon Larissa (2) | 1–0 | Xanthi (2) |
| 2021 | Ionikos (2) | 1–0 | Niki Volos (3) |
| 2021 | Panathinaikos (1) | 2–0 | Panetolikos (1) |
| 2021 | Aspropyrgos (3) | 0–1 | AEL (1) |
| 2021 | Volos (1) | 0–0 (a.e.t.) (2–1 p) | Panachaiki (2) |
| 2021 | PAS Giannina (1) | 1–2 | Doxa Drama (2) |
| 2021 | Apollon Smyrnis (1) | 0–2 | Asteras Tripolis (1) |
| 2021 | Levadiakos (2) | 0–1 | AEP Kozani (3) |
| 2021 | Karaiskakis (2) | 1–0 | O.F. Ierapetra (2) |
Round of 16
edit| 2021 | Asteras Tripolis (1) | 1–2 | Olympiacos (1) |
| 2021 | AEP Kozani (3) | 2–3 | Panathinaikos (1) |
| 2021 | Lamia (1) | 1–0 | Karaiskakis (2) |
| 2021 | AEK Athens (1) | 1–0 | Apollon Larissa (2) |
| 2021 | Doxa Drama (2) | 0–2 | PAOK (1) |
| 2021 | Aris Thessaloniki (1) | 0–1 | Ionikos (2) |
Quarterfinals
edit| 2021 | Olympiacos (1) | 1–0 (a.e.t.) | PAOK (1) |
| 2021 | AEK Athens (1) | 0–3 | Panathinaikos (1) |
Semifinals
edit| 2021 | Olympiacos (1) | 1–0 | Ionikos (2) |
| 2021 | OFI (1) | 0–1 | Panathinaikos (1) |
Final
edit| Olympiacos (1) | 1–0 | Panathinaikos (1) |
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