| Date | League | Home | Results | Away | HT | HDP | W/L |
|---|---|---|---|---|---|---|---|
| 2026-01-03 23:00 | Greek Super Cup | OFI Crete | 0:0 | Olympiakos Piraeus | 0:0 | -1.75 | Win |
| 2025-12-06 23:00 | Greek Super Cup | Olympiakos Piraeus | 3:0 | OFI Crete | 2:0 | 2.5 | Lose |
| 2025-05-18 00:00 | Greek Super Cup | OFI Crete | 0:0 | Olympiakos Piraeus | 0:0 | ||
| 2025-03-10 01:00 | Greek Super Cup | Olympiakos Piraeus | 1:0 | OFI Crete | 1:0 | 2 | Win |
| 2024-12-01 23:00 | Greek Super Cup | OFI Crete | 0:2 | Olympiakos Piraeus | 0:0 | -1.25 | Lose |
| 2024-02-10 23:30 | Greek Super Cup | Olympiakos Piraeus | 4:0 | OFI Crete | 3:0 | 1.75 | Lose |
| 2023-10-31 03:30 | Greek Super Cup | OFI Crete | 0:2 | Olympiakos Piraeus | 0:1 | -1 | Lose |
| 2023-01-29 22:00 | Greek Super Cup | Olympiakos Piraeus | 2:1 | OFI Crete | 1:1 | 1.5 | Win |
| 2022-10-09 21:00 | Greek Super Cup | OFI Crete | 1:2 | Olympiakos Piraeus | 1:0 | -1 | Draw |
| 2022-02-28 01:30 | Greek Super Cup | Olympiakos Piraeus | 2:0 | OFI Crete | 1:0 | 1.25 | Lose |
| 2021-12-05 01:30 | Greek Super Cup | OFI Crete | 1:3 | Olympiakos Piraeus | 1:1 | -1 | Lose |
| 2021-02-07 23:15 | Greek Super Cup | Olympiakos Piraeus | 3:0 | OFI Crete | 2:0 | 1.5 | Lose |
| 2020-11-08 21:00 | Greek Super Cup | OFI Crete | 0:2 | Olympiakos Piraeus | 0:0 | -1.5 | Lose |
| 2020-07-16 00:15 | Greek Super Cup | OFI Crete | 1:3 | Olympiakos Piraeus | 0:2 | -1.25 | Lose |
| 2020-07-02 02:30 | Greek Super Cup | Olympiakos Piraeus | 2:1 | OFI Crete | 1:1 | 1.75 | Win |
| Date | League | Home | Results | Away | HT | HDP | W/L |
|---|---|---|---|---|---|---|---|
| 2026-02-05 00:00 | Greek Super Cup | OFI Crete | 0:0 | Levadiakos | 0:0 | ||
| 2026-01-14 23:00 | Greek Super Cup | AEK Athens | 0:1 | OFI Crete | 0:0 | 2 | Win |
| 2026-01-07 23:00 | Greek Super Cup | OFI Crete | 2:0 | Asteras Tripolis | 1:0 | 0 | Lose |
| 2025-12-03 23:30 | Greek Super Cup | AEK Athens | 2:0 | OFI Crete | 1:0 | 1.75 | Lose |
| 2025-10-28 22:00 | Greek Super Cup | OFI Crete | 3:1 | Iraklis | 1:1 | 1 | Lose |
| 2025-09-24 20:00 | Greek Super Cup | Kallithea | 0:1 | OFI Crete | 0:1 | -1 | Draw |
| 2025-09-17 21:00 | Greek Super Cup | OFI Crete | 3:0 | AO Kavala | 2:0 | 2 | Lose |
| 2026-02-08 00:00 | Greek Super Cup | OFI Crete | 0:0 | Levadiakos | 0:0 | ||
| 2026-02-01 00:00 | Greek Super Cup | Atromitos Athens | 0:0 | OFI Crete | 0:0 | ||
| 2026-01-25 23:30 | Greek Super Cup | OFI Crete | 0:0 | Panaitolikos Agrinio | 0:0 | ||
| 2026-01-19 01:00 | Greek Super Cup | PAOK Saloniki | 3:0 | OFI Crete | 3:0 | 2.25 | Lose |
| 2026-01-11 23:30 | Greek Super Cup | OFI Crete | 4:0 | Asteras Tripolis | 2:0 | 0 | Lose |
| 2025-12-22 03:00 | Greek Super Cup | AEK Athens | 2:1 | OFI Crete | 0:1 | 1.75 | Win |
| 2025-12-14 00:00 | Greek Super Cup | OFI Crete | 3:0 | Panserraikos | 3:0 | 0.75 | Lose |
| 2025-11-29 23:30 | Greek Super Cup | OFI Crete | 0:1 | Volos NFC | 0:0 | 0 | Win |
| 2025-11-25 02:00 | Greek Super Cup | AEL Larisa | 1:2 | OFI Crete | 1:2 | 0.25 | Win |
| 2025-11-09 23:30 | Greek Super Cup | OFI Crete | 0:1 | AEK Athens | 0:0 | -1.25 | Lose |
| 2025-11-03 23:00 | Greek Super Cup | Asteras Tripolis | 3:0 | OFI Crete | 1:0 | 0.25 | Lose |
| 2025-10-26 01:00 | Greek Super Cup | OFI Crete | 1:3 | Atromitos Athens | 1:1 | 0.5 | Win |
| 2025-10-19 01:00 | Greek Super Cup | Panaitolikos Agrinio | 4:2 | OFI Crete | 0:0 | -0.25 | Lose |
| 2025-10-04 23:00 | Greek Super Cup | OFI Crete | 3:0 | Aris Thessaloniki | 1:0 | -0.25 | Lose |
| 2025-09-29 00:00 | Greek Super Cup | OFI Crete | 1:3 | AE Kifisias | 0:1 | 0.5 | Win |
| 2025-09-21 23:00 | Greek Super Cup | Levadiakos | 4:0 | OFI Crete | 1:0 | 0.25 | Lose |
| 2025-09-15 02:30 | Greek Super Cup | OFI Crete | 1:2 | PAOK Saloniki | 0:2 | -0.75 | Win |
| 2025-08-31 00:30 | Greek Super Cup | Panserraikos | 0:1 | OFI Crete | 0:0 | 0 | Win |
| 2025-08-25 00:45 | Greek Super Cup | Panathinaikos | 0:0 | OFI Crete | 0:0 | 1.5 | Win |
| 2025-05-11 00:15 | Greek Super Cup | Atromitos Athens | 0:0 | OFI Crete | 0:0 | 0.5 | Win |
| 2025-05-04 01:00 | Greek Super Cup | OFI Crete | 1:1 | Aris Thessaloniki | 1:0 | -0.25 | Lose |
| 2025-04-27 01:00 | Greek Super Cup | OFI Crete | 0:2 | Asteras Tripolis | 0:0 | 0 | Win |
| 2025-04-13 21:30 | Greek Super Cup | Asteras Tripolis | 2:1 | OFI Crete | 1:1 | 0.25 | Lose |
| Date | League | Home | Results | Away | HT | HDP | W/L |
|---|---|---|---|---|---|---|---|
| 2026-01-15 00:30 | Greek Super Cup | Olympiakos Piraeus | 0:2 | PAOK Saloniki | 0:2 | 0.75 | Win |
| 2025-12-18 00:00 | Greek Super Cup | Olympiakos Piraeus | 6:0 | Iraklis | 4:0 | 2.75 | Lose |
| 2025-12-03 19:30 | Greek Super Cup | Hellas Syrou | 2:5 | Olympiakos Piraeus | 0:1 | -2.5 | Win |
| 2025-10-29 23:30 | Greek Super Cup | Olympiakos Piraeus | 5:0 | Volos NFC | 4:0 | 1.75 | Lose |
| 2025-09-24 22:00 | Greek Super Cup | Asteras Tripolis | 1:2 | Olympiakos Piraeus | 0:2 | -1 | Draw |
| 2025-12-09 23:30 | Greek Super Cup | FC Kairat Almaty | 0:1 | Olympiakos Piraeus | 0:0 | -0.75 | Win |
| 2025-09-18 00:45 | Greek Super Cup | Olympiakos Piraeus | 0:0 | AEP Paphos | 0:0 | 1 | Win |
| 2026-01-29 04:00 | Greek Super Cup | AFC Ajax | 0:0 | Olympiakos Piraeus | 0:0 | ||
| 2025-11-05 04:00 | Greek Super Cup | Olympiakos Piraeus | 1:1 | PSV Eindhoven | 1:0 | 0.25 | Win |
| 2026-01-21 04:00 | Greek Super Cup | Olympiakos Piraeus | 2:0 | Bayer Leverkusen | 2:0 | 0 | Lose |
| 2025-10-02 03:00 | Greek Super Cup | Arsenal | 2:0 | Olympiakos Piraeus | 1:0 | 1.75 | Lose |
| 2025-10-22 00:45 | Greek Super Cup | FC Barcelona | 6:1 | Olympiakos Piraeus | 2:0 | 2 | Lose |
| 2025-11-27 04:00 | Greek Super Cup | Olympiakos Piraeus | 3:4 | Real Madrid | 1:3 | -1.25 | Lose |
| 2026-02-08 00:00 | Greek Super Cup | Olympiakos Piraeus | 0:0 | Panathinaikos | 0:0 | ||
| 2026-02-02 03:00 | Greek Super Cup | AEK Athens | 0:0 | Olympiakos Piraeus | 0:0 | ||
| 2026-01-24 23:00 | Greek Super Cup | Olympiakos Piraeus | 0:0 | Volos NFC | 0:0 | 2 | Win |
| 2026-01-11 01:30 | Greek Super Cup | Atromitos Athens | 0:2 | Olympiakos Piraeus | 0:1 | -1.5 | Win |
| 2025-12-21 02:30 | Greek Super Cup | Olympiakos Piraeus | 1:1 | AE Kifisias | 1:1 | 2.25 | Win |
| 2025-12-15 02:00 | Greek Super Cup | Aris Thessaloniki | 0:0 | Olympiakos Piraeus | 0:0 | -1 | Lose |
| 2025-11-30 23:00 | Greek Super Cup | Panaitolikos Agrinio | 0:1 | Olympiakos Piraeus | 0:0 | -1.75 | Lose |
| 2025-11-23 02:00 | Greek Super Cup | Olympiakos Piraeus | 3:0 | Atromitos Athens | 1:0 | 2.25 | Lose |
| 2025-11-09 21:00 | Greek Super Cup | AE Kifisias | 1:3 | Olympiakos Piraeus | 0:1 | -1.5 | Win |
| 2025-11-02 02:00 | Greek Super Cup | Olympiakos Piraeus | 2:1 | Aris Thessaloniki | 0:0 | 1.25 | Win |
| 2025-10-27 03:00 | Greek Super Cup | Olympiakos Piraeus | 2:0 | AEK Athens | 1:0 | 0.75 | Lose |
| 2025-10-18 22:00 | Greek Super Cup | AEL Larisa | 0:2 | Olympiakos Piraeus | 0:2 | -1.5 | Win |
| 2025-10-06 01:30 | Greek Super Cup | PAOK Saloniki | 2:1 | Olympiakos Piraeus | 0:1 | 0 | Lose |
| 2025-09-27 23:00 | Greek Super Cup | Olympiakos Piraeus | 3:2 | Levadiakos | 1:0 | 1.75 | Win |
| 2025-09-22 02:00 | Greek Super Cup | Panathinaikos | 1:1 | Olympiakos Piraeus | 0:0 | -0.25 | Lose |
| 2025-09-13 23:00 | Greek Super Cup | Olympiakos Piraeus | 5:0 | Panserraikos | 0:0 | 2.25 | Lose |
| 2025-08-31 00:00 | Greek Super Cup | Volos NFC | 0:2 | Olympiakos Piraeus | 0:0 | -1.75 | Win |
