| 1. Round | 18/10/2020 | UD Melilla | - | CP Villarrobledo | 3:0 |  |
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| 2. Round | 25/10/2020 | CP Villarrobledo | - | UD Socuéllamos | 0:0 | |
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| 3. Round | 01/11/2020 | Don Benito | - | CP Villarrobledo | 1:0 | |
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| 4. Round | 08/11/2020 | CP Villarrobledo | - | Extremadura UD | 0:1 | ||||
| 5. Round | 22/11/2020 | CD Badajoz | - | CP Villarrobledo | 5:3 |  |
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| 6. Round | 29/11/2020 | CP Villarrobledo | - | Villarrubia CF | 1:2 | ||||
| 7. Round | 06/12/2020 | CP Villarrobledo | - | CF Talavera | 3:2 | |
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| 11. Round | 24/01/2021 | UD Socuéllamos | - | CP Villarrobledo | 1:0 | ||||
| 14. Round | 14/02/2021 | CP Villarrobledo | - | CD Badajoz | 0:0 | |
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| 15. Round | 21/02/2021 | Villarrubia CF | - | CP Villarrobledo | 1:1 | |
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| 16. Round | 07/03/2021 | CF Talavera | - | CP Villarrobledo | 2:1 | ||||
| 17. Round | 13/03/2021 | CP Villarrobledo | - | CF Villanovense | 1:2 | ||||
| 18. Round | 21/03/2021 | Mérida AD | - | CP Villarrobledo | 0:1 |
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