| ITF - W25 Santa Margherita | 09/26 12:00 | 26 | [483] Tatiana Pieri v Deborah Chiesa [371] | 7-6,5-7,6-0 | |
| ITF - W25 Santa Margherita | 09/25 14:35 | 25 | [485] Linnea Malmqvist v Deborah Chiesa [371] | 1-6,3-6 | |
| ITF - W25 Santa Margherita | 09/18 14:00 | 25 | [362] Deborah Chiesa v Camilla Scala [444] | 6-2,6-7,1-6 | |
| ITF - W25 Trieste | 09/04 12:30 | 25 | Corinna Dentoni v Deborah Chiesa | 2-6,6-4,6-3 | |
| ITF - W25 Verbier | 08/27 09:15 | 25 | [352] Deborah Chiesa v Kathinka Von Deichmann [293] | 2-6,4-6 | |
| ITF - W25 LPD Gran Canaria | 08/14 09:00 | 25 | [352] Deborah Chiesa v Alexandra Bozovic [392] | 4-6,6-2,2-6 | |
| ITF W60 Warsaw | 08/09 09:30 | 27 | [359] Deborah Chiesa v Yue Yuan [272] | 3-6,6-3,5-7 | |
| ITF W60 Warsaw | 08/08 12:30 | 26 | [359] Deborah Chiesa v Vivien Juhaszova [391] | Retired | |
| ITF W60 Warsaw | 08/06 11:45 | 25 | Isabella Shinikova v Deborah Chiesa | 4-6,2-6 | |
| ITF W25 Sezze | 08/01 12:30 | 26 | Maria Marfutina v Deborah Chiesa | 6-1,2-6,6-1 | |
| ITF W25 Sezze | 07/30 15:30 | 25 | [437] Melanie Klaffner v Deborah Chiesa [349] | 2-6,7-6,3-6 | |
| WTA - Palermo | 07/20 16:40 | 45 | [336] Deborah Chiesa v Amandine Hesse [251] | 6-1,4-6,5-7 | |
| ITF W25 Imola | 07/18 17:30 | 26 | Deborah Chiesa v Corinna Dentoni | 4-6,1-6 | |
| ITF W25 Imola | 07/17 15:35 | 25 | Deborah Chiesa v Martina Spigarelli | 6-4,3-6,7-6 | |
| ITF - W25 Torino | 07/11 08:30 | 26 | [380] Angelica Moratelli v Deborah Chiesa [314] | 5-7,7-5,6-3 | |
| ITF - W25 Torino | 07/10 11:55 | 25 | Gabriella Da Silva Fick v Deborah Chiesa | 2-6,3-6 | |
| ITF W25 Biella | 07/02 18:05 | 25 | Deborah Chiesa v Maiar S A Abdelaziz | 2-6,3-6 | |
| ITF W25 Biella | 07/02 15:00 | - | [314] Deborah Chiesa v Maiar Sherif [500] | 2-6,3-6 | |
| ITF - W25 Tarvisio | 06/27 13:45 | 26 | [313] Deborah Chiesa v Miriam B Bulgaru [454] | 5-7,1-6 | |
| ITF - W25 Tarvisio | 06/26 15:30 | 25 | [300] Chihiro Muramatsu v Deborah Chiesa [313] | 4-6,7-5,3-6 | |
| ITF - W25 Tarvisio | 06/25 11:10 | 54 | [313] Deborah Chiesa v Angelica Moratelli [463] | 6-1,6-0 | |
| ITF W25 Padova | 06/20 13:30 | 26 | Deborah Chiesa v Bianca Turati | 2-6,1-6 | |
| ITF W25 Padova | 06/18 18:35 | 25 | Deborah Chiesa v Barbora Matusova | 3-6,6-1,6-2 | |
| ITF - W60 Roma | 06/10 14:00 | 45 | [315] Deborah Chiesa v Tatiana Pieri [465] | 1-6,5-7 | |
| ITF - W60 Brescia | 06/08 14:00 | 28 | [322] Deborah Chiesa v Diana Marcinkevica [268] | 7-6,6-7,6-7 | |
| ITF - W60 Brescia | 06/07 12:35 | 27 | [183] Barbara Haas v Deborah Chiesa [322] | 6-7,5-7 | |
| ITF - W60 Brescia | 06/06 13:00 | 26 | [322] Deborah Chiesa v Francesca Di Lorenzo [154] | 6-2,6-2 | |
| ITF - W60 Brescia | 06/04 13:40 | 25 | Deborah Chiesa v Romina Oprandi | Retired | |
| ITF - W25 Grado | 05/31 08:00 | 26 | [198] Rebecca Sramkova v Deborah Chiesa [322] | 5-7,7-6,6-4 | |
| ITF - W25 Grado | 05/30 09:00 | 25 | [322] Deborah Chiesa v Anna Danilina [360] | 6-1,7-5 |