| 1 | Sun 4 Aug 2019 | 0-4 v sc HeerenveenHeracles Almelo 0-4 sc Heerenveen |
| 2 | Sun 11 Aug 2019 | 1-1 v Fortuna SittardFortuna Sittard 1-1 Heracles Almelo |
| 3 | Sun 18 Aug 2019 | 0-2 v PSV EindhovenHeracles Almelo 0-2 PSV Eindhoven |
| 4 | Sat 24 Aug 2019 | 1-1 v VitesseHeracles Almelo 1-1 Vitesse |
| 5 | Sat 31 Aug 2019 | 2-1 v FC GroningenFC Groningen 1-2 Heracles Almelo |
| 6 | Sun 15 Sep 2019 | 4-1 v Willem IIHeracles Almelo 4-1 Willem II |
| 7 | Fri 20 Sep 2019 | 3-2 v FC TwenteFC Twente 2-3 Heracles Almelo |
| 8 | Sun 29 Sep 2019 | 0-2 v AZ AlkmaarAZ Alkmaar 2-0 Heracles Almelo |
| 9 | Sat 5 Oct 2019 | 2-0 v FC EmmenHeracles Almelo 2-0 FC Emmen |
| 10 | Sun 20 Oct 2019 | 1-1 v FeyenoordFeyenoord 1-1 Heracles Almelo |
| 11 | Sat 26 Oct 2019 | 4-0 v PEC ZwolleHeracles Almelo 4-0 PEC Zwolle |
| 12 | Sat 2 Nov 2019 | 0-2 v RKC WaalwijkRKC Waalwijk 2-0 Heracles Almelo |
| 13 | Sat 9 Nov 2019 | 6-1 v VVV VenloHeracles Almelo 6-1 VVV Venlo |
| 14 | Sat 23 Nov 2019 | 1-4 v AjaxAjax 4-1 Heracles Almelo |
| 15 | Sat 30 Nov 2019 | 4-0 v ADO Den HaagHeracles Almelo 4-0 ADO Den Haag |
| 16 | Sun 8 Dec 2019 | 0-0 v Sparta RotterdamSparta Rotterdam 0-0 Heracles Almelo |
| 17 | Sun 15 Dec 2019 | 1-3 v FC UtrechtHeracles Almelo 1-3 FC Utrecht |
| 18 | Sat 21 Dec 2019 | 1-1 v sc Heerenveensc Heerenveen 1-1 Heracles Almelo |
| 19 | Sun 19 Jan 2020 | 0-1 v FC EmmenFC Emmen 1-0 Heracles Almelo |
| 20 | Sat 25 Jan 2020 | 2-3 v FeyenoordHeracles Almelo 2-3 Feyenoord |
| 21 | Sun 2 Feb 2020 | 0-1 v Willem IIWillem II 1-0 Heracles Almelo |
| 22 | Sun 23 Feb 2020 | 1-0 v AjaxHeracles Almelo 1-0 Ajax |
| 23 | Sat 29 Feb 2020 | 0-0 v ADO Den HaagADO Den Haag 0-0 Heracles Almelo |
| 24 | Sun 8 Mar 2020 | 4-2 v RKC WaalwijkHeracles Almelo 4-2 RKC Waalwijk |
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