| ITF - W25 Solarino | 11/08 08:00 | 25 | Diletta Cherubini v Arianna Zucchini | 6-2,7-6 | |
| ITF - W25 Solarino | 10/31 09:30 | 25 | [189] Ylena In-Albon v Diletta Cherubini [498] | Retired | |
| ITF - W25 Santa Margherita | 09/27 08:30 | 25 | [474] Diletta Cherubini v Ekaterine Gorgodze [381] | Retired | |
| ITF - W25 Santa Margherita | 09/22 09:00 | 27 | [469] Diletta Cherubini v Katharina Hobgarski [316] | 1-6,2-6 | |
| ITF - W25 Santa Margherita | 09/21 11:35 | 26 | [412] Tina Nadine Smith v Diletta Cherubini [469] | 6-7,6-4,6-7 | |
| ITF - W25 Santa Margherita | 09/20 11:15 | 25 | Diletta Cherubini v Denise Valente | 6-0,6-4 | |
| 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 08:30 | 26 | Laura Hietaranta v Diletta Cherubini | 6-2,3-6,5-7 | |
| ITF - W25 Zaragoza | 09/05 11:15 | 25 | Maileen Nuudi v Diletta Cherubini | Retired | |
| ITF - W25 Trieste | 08/31 11:40 | 26 | [441] Angela Fita Boluda v Diletta Cherubini [470] | 7-5,7-5 | |
| ITF - W25 Trieste | 08/30 12:20 | 25 | [470] Diletta Cherubini v Lisa Pigato [465] | Retired | |
| ITF - W60 Prerov | 08/22 10:25 | 54 | [485] Diletta Cherubini v Andreea Mitu [268] | 3-6,1-6 | |
| ITF - W60 Prerov | 08/21 14:15 | 54 | [485] Diletta Cherubini v Tayisiya Morderger [466] | 6-3,6-0 | |
| ITF - W25 Vrnjacka Banja | 08/17 07:30 | 26 | [257] Tena Lukas v Diletta Cherubini [484] | 6-1,6-1 | |
| ITF - W25 Vrnjacka Banja | 08/16 14:00 | 25 | Diletta Cherubini v Elena Milovanovic | 6-1,6-1 | |
| ITF - W60 Cordenons | 08/01 14:35 | 25 | [475] Diletta Cherubini v Rasheeda McAdoo [283] | 0-6,3-6 | |
| ITF - W60 Roma | 07/13 12:55 | 26 | [475] Diletta Cherubini v Irene Burillo Escorihuela [241] | 6-1,6-7,2-6 | |
| ITF - W60 Roma | 07/12 14:00 | 25 | Julia Terziyska v Diletta Cherubini | 2-6,6-0,2-6 | |
| ITF - W25 Getxo | 07/07 10:00 | 27 | [437] Lucia Cortez Llorca v Diletta Cherubini [475] | 1-6,6-4,6-0 | |
| ITF - W25 Getxo | 07/05 11:50 | 26 | [475] Diletta Cherubini v Adithya Karunaratne [369] | 7-6,6-2 | |
| ITF - W25 Getxo | 07/04 09:00 | 25 | [475] Diletta Cherubini v Ilay Yoruk [480] | 2-6,6-4,6-2 | |
| ITF - W25 Tarvisio | 06/27 10:30 | 25 | [251] Alexandra Ignatik v Diletta Cherubini [469] | 6-7,6-1,6-4 | |
| ITF - W40 Otocec | 05/31 12:05 | 25 | [270] Elvina Kalieva v Diletta Cherubini [415] | 6-0,6-2 | |
| ITF - W40 Otocec | 05/29 12:15 | 24 | [415] Diletta Cherubini v Radka Zelnickova [394] | 6-2,6-1 | |
| WTA - Florenta | 05/16 14:50 | 25 | [421] Diletta Cherubini v Eugenie Bouchard [233] | 4-6,4-6 | |
| WTA - Roma | 05/09 11:45 | 23 | [421] Diletta Cherubini v Lisa Pigato [483] | 5-7,6-2,3-6 | |
| ITF - W25 Santa Margherita | 05/03 15:25 | 25 | Diletta Cherubini v Federica Bilardo | 6-4,4-6,2-6 | |
| ITF - W25 Osijek | 04/26 08:00 | 25 | [411] Diletta Cherubini v Lucie Havlickova [277] | 4-6,1-6 | |
| ITF - W60 Koper | 04/18 10:50 | 24 | [411] Diletta Cherubini v Suzan Lamens [285] | 4-6,4-6 | |
| ITF - W25 Santa Margherita | 04/13 10:15 | 26 | [209] Katharina Hobgarski v Diletta Cherubini [414] | 6-3,6-4 |