| 23 Sep 23 | r01        | Makedonikos NeapolisMakedonikos N | 0 - 0 | Iraklis 1908Iraklis 1908 |
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| 01 Oct 23 | r02        | Iraklis 1908Iraklis 1908 | 1 - 1 | Anagennisi KarditsasAnagennisi Ka |
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| 11 Oct 23 | r03        | AE LarissaAE Larissa | 1 - 0 | Iraklis 1908Iraklis 1908 |
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| 22 Oct 23 | r05        | AlmoposAlmopos | - | Iraklis 1908Iraklis 1908 |
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| 25 Oct 23 | r04        | Iraklis 1908Iraklis 1908 | 2 - 0 | PAOK IIPAOK II |
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| 04 Nov 23 | r07        | Iraklis 1908Iraklis 1908 | 0 - 1 | LevadeiakosLevadeiakos |
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| 12 Nov 23 | r08        | Niki VolouNiki Volou | 3 - 1 | Iraklis 1908Iraklis 1908 |
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| 15 Nov 23 | r09        | Iraklis 1908Iraklis 1908 | 0 - 1 | Apollon PontouApollon Ponto |
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| 25 Nov 23 | r11        | Iraklis 1908Iraklis 1908 | 1 - 0 | AEK Athens IIAEK Athens II |
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| 18 Dec 23 | r14        | Iraklis 1908Iraklis 1908 | 5 - 1 | Makedonikos NeapolisMakedonikos N |
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| 03 Jan 24 | r15        | Anagennisi KarditsasAnagennisi Ka | 2 - 1 | Iraklis 1908Iraklis 1908 |
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| 07 Jan 24 | r16        | Iraklis 1908Iraklis 1908 | 1 - 1 | AE LarissaAE Larissa |
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| 15 Jan 24 | r17        | PAOK IIPAOK II | 1 - 1 | Iraklis 1908Iraklis 1908 |
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| 21 Jan 24 | r18        | Iraklis 1908Iraklis 1908 | - | AlmoposAlmopos |
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| 04 Feb 24 | r20        | LevadeiakosLevadeiakos | 2 - 0 | Iraklis 1908Iraklis 1908 |
| |
| 11 Feb 24 | r21        | Iraklis 1908Iraklis 1908 | 1 - 0 | Niki VolouNiki Volou |
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| 14 Feb 24 | r22        | Apollon PontouApollon Ponto | 0 - 1 | Iraklis 1908Iraklis 1908 |
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| 25 Feb 24 | r24        | AEK Athens IIAEK Athens II | 0 - 0 | Iraklis 1908Iraklis 1908 |
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| 03 Apr 24 | r03        | Anagennisi KarditsasAnagennisi Ka | 0 - 0 | Iraklis 1908Iraklis 1908 |
| |
| 07 Apr 24 | r04        | Iraklis 1908Iraklis 1908 | 2 - 1 | PAOK IIPAOK II |
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| 08 May 24 | r08        | Iraklis 1908Iraklis 1908 | 0 - 0 | Anagennisi KarditsasAnagennisi Ka |
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| 14 May 24 | r09        | PAOK IIPAOK II | 2 - 2 | Iraklis 1908Iraklis 1908 |