| WTA Buenos Aires | 11/28 14:00 | 25 | [382] Guillermina Naya v Valeriya Strakhova [280] | Retired | |
| WTA Colina | 11/16 16:00 | 26 | [159] Yulia Starodubtsewa v Guillermina Naya [402] | 6-2,6-0 | |
| WTA Colina | 11/15 15:00 | 25 | [325] Sada Nahimana v Guillermina Naya [402] | 2-6,1-6 | |
| ITF W25 Monastir | 11/01 13:35 | 25 | Guillermina Naya v Anastasia Sukhotina | 2-6,3-6 | |
| ITF W25 Santa Margherita | 10/29 12:50 | 29 | [139] Brenda Fruhvirtova v Guillermina Naya [461] | 6-4,6-3 | |
| ITF W25 Santa Margherita | 10/29 09:00 | 28 | [461] Guillermina Naya v Martina Colmegna [407] | 6-2,6-1 | |
| ITF W25 Santa Margherita | 10/28 11:15 | 27 | Guillermina Naya v Anna Turati | 6-2,6-3 | |
| ITF W25 Santa Margherita | 10/28 08:00 | 26 | [319] Leyre Romero Gormaz v Guillermina Naya [461] | 3-6,4-6 | |
| ITF W25 Santa Margherita | 10/24 11:05 | 25 | Guillermina Naya v Paola Lopez | 6-1,6-1 | |
| ITF W25 Seville | 10/13 10:50 | 28 | [392] Lois Boisson v Guillermina Naya [424] | 5-7,6-1,6-4 | |
| ITF W25 Seville | 10/12 07:45 | 27 | [424] Guillermina Naya v Aneta Kucmova [427] | 6-3,7-5 | |
| ITF W25 Seville | 10/11 08:30 | 26 | [285] Isabella Shinikova v Guillermina Naya [424] | 3-6,3-6 | |
| ITF W25 Seville | 10/10 12:10 | 25 | [424] Guillermina Naya v Angela Fita Boluda [489] | Retired | |
| ITF W25 Seville | 10/09 08:00 | 44 | Guillermina Naya v Gyeong Seo Lee | 6-2,6-0 | |
| ITF W25 Seville | 10/08 13:30 | 44 | Guillermina Naya v Laura Boehner | 6-1,6-3 | |
| ITF W25 Slobozia | 09/20 07:00 | 25 | [419] Guillermina Naya v Ella Seidel [266] | 7-6,3-6,2-6 | |
| ITF W25 Slobozia | 09/19 07:00 | 62 | Guillermina Naya v Chiara Fornasieri | 6-1,7-5 | |
| ITF W25 Slobozia | 09/18 10:35 | 62 | Guillermina Naya v Maria Theodora Stancescu | 6-1,6-2 | |
| ITF W25 Leiria | 09/13 13:35 | 25 | Angelina Voloshchuk v Guillermina Naya | 6-1,6-2 | |
| ITF W25 Zaragoza | 09/09 09:30 | 29 | [434] Guillermina Naya v Solana Sierra [255] | 6-4,2-6,2-6 | |
| ITF W25 Zaragoza | 09/08 10:30 | 28 | [434] Guillermina Naya v Ashley Lahey [362] | 1-6,6-4,6-2 | |
| ITF W25 Zaragoza | 09/07 14:00 | 27 | [434] Guillermina Naya v Diletta Cherubini [470] | 6-7,6-4,6-2 | |
| ITF W25 Zaragoza | 09/06 12:40 | 26 | [203] Victoria J Kasintseva v Guillermina Naya [434] | 6-0,4-6,2-6 | |
| ITF W25 Zaragoza | 09/05 09:55 | 25 | Olga Saez Larra v Guillermina Naya | 0-6,0-6 | |
| WTA Cleveland | 08/19 17:20 | 14 | [77] Magdalena Frech v Guillermina Naya [434] | 6-0,6-1 | |
| ITF W40 Arequipa | 08/17 17:10 | 26 | [434] Guillermina Naya v Jana Kolodynska [260] | 3-6,3-6 | |
| ITF W40 Arequipa | 08/16 16:00 | 25 | [434] Guillermina Naya v Jaeda Daniel [330] | 6-3,6-7,6-3 | |
| ITF W25 Junin | 08/02 13:00 | 25 | Luciana Blatter v Guillermina Naya | 7-5,6-3 | |
| ITF W25 Bragado | 07/28 15:30 | 27 | [445] Guillermina Naya v Solana Sierra [290] | 4-6,7-5,3-6 | |
| ITF W25 Bragado | 07/27 15:20 | 26 | Guillermina Naya v Lourdes Ayala | 6-3,6-2 |