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| 15.03.2019 | D2 | Anagennisi Derynia | 1-2 | Olympiakos Nicosia | |
| 24.11.2018 | D2 | Olympiakos Nicosia | 4-1 | Anagennisi Derynia | |
| 29.11.2017 | Cup | Olympiakos Nicosia | 3-0 | Anagennisi Derynia | |
| 26.03.2016 | D2 | Olympiakos Nicosia | 1-1 | Anagennisi Derynia | |
| 12.12.2015 | D2 | Anagennisi Derynia | 2-0 | Olympiakos Nicosia | |
| 14.03.2015 | D2 | Anagennisi Derynia | 1-1 | Olympiakos Nicosia |
| GP | W | D | L | GF | GA | +/- | |
| home | 6 | 2 | 2 | 2 | 11 | 9 | 2 |
| away | 6 | 1 | 0 | 5 | 8 | 14 | -6 |
| total | 6 | 3 | 0 | 3 | 10 | 8 | 2 |
| Anagennisi Der. win | 35.29% | 6 |
| draw | 23.53% | 4 |
| Anagennisi Der. lose | 41.18% | 7 |
| GP | W | D | L | GF | GA | +/- | |
| home | 6 | 2 | 2 | 2 | 10 | 6 | 4 |
| away | 6 | 2 | 2 | 2 | 5 | 6 | -1 |
| total | 6 | 2 | 2 | 2 | 4 | 5 | -1 |
| Olympiakos CYP win | 41.18% | 7 |
| draw | 23.53% | 4 |
| Olympiakos CYP lose | 35.29% | 6 |
| 14.12.2024 | D2 | ENY Digenis Ypsonas | 1-0 | Anagennisi Derynia |  |
| 07.12.2024 | D2 | Anagennisi Derynia | 4-1 | Peyia 2014 |  |
| 01.12.2024 | D2 | ASIL Lysi | 3-0 | Anagennisi Derynia | |
| 23.11.2024 | D2 | Anagennisi Derynia | 1-0 | AEZ Zakakiou | |
| 09.11.2024 | D2 | MEAP Nisou | 1-4 | Anagennisi Derynia | |
| 06.11.2024 | Cup | Anagennisi Derynia | 1-2 | EN Paralimni | |
| 14.12.2024 | D2 | ASIL Lysi | 0-2 | Olympiakos Nicosia | |
| 07.12.2024 | D2 | Olympiakos Nicosia | 0-0 | AEZ Zakakiou |  |
| 30.11.2024 | D2 | MEAP Nisou | 3-0 | Olympiakos Nicosia | |
| 23.11.2024 | D2 | Olympiakos Nicosia | 1-2 | Digenis Morfou | |
| 08.11.2024 | D2 | Halkanoras Idaliou | 0-1 | Olympiakos Nicosia | |
| 01.11.2024 | D2 | Olympiakos Nicosia | 0-0 | Akritas Chlorakas | |
| over 2.5 | 71.43% | 10 |
| under 2.5 | 28.57% | 4 |
| over 2.5 | 46.15% | 6 |
| under 2.5 | 53.85% | 7 |
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