| ITF Women Santa Margherita | 09/12 14:10 | 25 | [479] Tayisiya Morderger v Deborah Chiesa [198] | 1-6,2-6 | |
| ITF Women Montreux | 09/04 12:55 | 25 | [301] Diana Marcinkevica v Deborah Chiesa [189] | 6-4,6-2 | |
| ITF Women Bagnatica | 08/30 10:30 | 26 | [273] Chloe Paquet v Deborah Chiesa [189] | 6-3,5-7,6-1 | |
| ITF Women Bagnatica | 08/29 14:55 | 25 | [308] Alize Lim v Deborah Chiesa [189] | 3-6,6-7 | |
| US Open - Kobiety | 08/22 18:10 | 44 | [179] Katie Swan v Deborah Chiesa [180] | 3-6,6-4,6-4 | |
| ITF Women Chiswick | 08/08 10:30 | 26 | [298] Pemra Ozgen v Deborah Chiesa [159] | 6-4,6-0 | |
| ITF Women Chiswick | 08/07 09:30 | 25 | Vlada Ekshibarova v Deborah Chiesa | 6-3,2-6,3-6 | |
| WTA Moskwa | 07/24 09:05 | 25 | Natalia Vikhlyantseva v Deborah Chiesa | 6-4,6-0 | |
| WTA Moscow Qual | 07/23 12:40 | 64 | [143] Deborah Chiesa v Sofya Lansere [494] | 7-6,6-0 | |
| WTA Moscow Qual | 07/22 11:20 | 45 | [143] Deborah Chiesa v Ekaterina Yashina [444] | 7-5,6-2 | |
| WTA Bucharest Qual | 07/14 07:00 | 45 | [148] Deborah Chiesa v Anna Bondar [393] | 2-6,1-6 | |
| ITF Women Contrexeville | 07/10 13:10 | 25 | [148] Deborah Chiesa v Mona Barthel [118] | 3-6,1-6 | |
| ITF Women Rome | 07/04 08:00 | 25 | [148] Deborah Chiesa v Anastasia Zarycka [315] | 4-6,1-6 | |
| Wimbledon Women Qual | 06/27 10:00 | 45 | [199] Mayo Hibi v Deborah Chiesa [148] | 6-3,6-1 | |
| Wimbledon Women Qual | 06/26 11:40 | 44 | [148] Deborah Chiesa v Carol Zhao [131] | 6-2,5-7,6-3 | |
| ITF Women Ilkley | 06/20 16:05 | 25 | [148] Deborah Chiesa v Tereza Smitkova [235] | 5-7,6-7 | |
| ITF Women Brescia | 06/05 15:00 | 25 | [358] Laura Siegemund v Deborah Chiesa [161] | 7-5,6-1 | |
| French Open - Kobiety | 05/28 13:50 | 23 | [72] Belinda Bencic v Deborah Chiesa [163] | 3-6,7-6,7-5 | |
| French Open Women Qual | 05/25 08:00 | 46 | [106] Arantxa Rus v Deborah Chiesa [163] | 6-7,2-6 | |
| French Open Women Qual | 05/24 09:35 | 45 | [163] Deborah Chiesa v Tamara Zidansek [123] | 6-4,7-5 | |
| French Open Women Qual | 05/23 08:00 | 44 | [163] Deborah Chiesa v Priscilla Hon [183] | 0-6,6-2,6-4 | |
| WTA Rome Qual | 05/12 14:20 | 45 | [166] Deborah Chiesa v Camila Giorgi [56] | 2-6,3-6 | |
| WTA Prague Qual | 04/29 09:00 | 46 | [160] Tereza Martincova v Deborah Chiesa [171] | 7-5,6-3 | |
| WTA Prague Qual | 04/28 09:45 | 45 | [171] Deborah Chiesa v Miriam Kolodziejova [316] | 5-7,6-2,6-2 | |
| WTA Lugano Qual | 04/08 09:00 | 45 | [220] Jessica Pieri v Deborah Chiesa [179] | 4-6,6-2,6-4 | |
| ITF Women Santa Margherita | 04/01 12:00 | 29 | [297] Mandy Minella v Deborah Chiesa [177] | 6-3,7-6 | |
| ITF Women Santa Margherita | 03/31 12:00 | 28 | [177] Deborah Chiesa v Valentyna Ivakhnenko [188] | 6-4,6-3 | |
| ITF Women Santa Margherita | 03/30 12:00 | 27 | [177] Deborah Chiesa v Federica Di Sarra [484] | 2-6,6-1,7-6 | |
| ITF Women Santa Margherita | 03/29 13:50 | 26 | [177] Deborah Chiesa v Katharina Hobgarski [276] | 3-6,6-4,6-4 | |
| ITF Women Santa Margherita | 03/28 18:10 | 25 | [177] Deborah Chiesa v Laura Schaeder [451] | 6-4,6-3 |