| ITF - W25 Santa Margherita | 04/12 08:30 | 25 | Diletta Cherubini v Sofia Rocchetti | 7-6,3-6,7-5 | |
| ITF - W25 Palmanova | 03/18 10:00 | 62 | Yeon Woo Ku v Diletta Cherubini | 6-4,6-4 | |
| ITF - W25 Palmanova | 03/13 08:00 | 62 | Diletta Cherubini v Emily Seibold | 4-6,3-6 | |
| ITF - W25 Palmanova | 03/12 10:00 | 62 | Diletta Cherubini v Marie Mettraux | 6-1,6-2 | |
| ITF - W25 Joue Les Tours | 02/27 12:20 | 54 | Diletta Cherubini v Tamira Paszek | 3-6,0-6 | |
| ITF - W25 Joue Les Tours | 02/26 14:45 | 54 | Diletta Cherubini v Anita Husaric | 6-3,6-0 | |
| ITF - W40 Macon | 02/22 09:00 | 25 | [175] Yuriko Lily Miyazaki v Diletta Cherubini [414] | 6-3,6-0 | |
| ITF - W40 Macon | 02/20 10:00 | 54 | Sara Cakarevic v Diletta Cherubini | 3-6,6-4,6-0 | |
| ITF - W40 Macon | 02/19 10:40 | 54 | Serafima Bobrovnikova v Diletta Cherubini | 5-7,2-6 | |
| ITF - W25 Antalya | 02/05 07:00 | 62 | Diletta Cherubini v Elena Korokozidi | 6-1,6-3 | |
| ITF - W25 Antalya | 02/02 08:30 | 26 | [268] Carlota M Cirez v Diletta Cherubini [422] | 6-3,6-1 | |
| ITF - W25 Antalya | 01/31 09:55 | 25 | [422] Diletta Cherubini v Elena-Teodora Cadar [387] | 2-6,6-1,6-2 | |
| ITF - W25 Monastir | 12/16 08:30 | 27 | Silvia Ambrosio v Diletta Cherubini | 4-6,6-3,6-3 | |
| ITF - W25 Monastir | 12/15 08:30 | 26 | [425] Diletta Cherubini v Sapfo Sakellaridi [310] | 6-4,6-2 | |
| ITF - W25 Monastir | 12/14 08:30 | 25 | [446] Oceane Babel v Diletta Cherubini [425] | 1-6,2-6 | |
| ITF - W25 Monastir | 12/07 11:40 | 25 | Diletta Cherubini v Fiona Ganz | 6-2,3-6,3-6 | |
| ITF - W25 Selva Gardena | 11/28 14:30 | 25 | [130] Clara Tauson v Diletta Cherubini [423] | 6-4,6-4 | |
| ITF - W80 Valencia | 11/21 14:35 | 54 | [271] Nuria Brancaccio v Diletta Cherubini [426] | 6-2,6-2 | |
| ITF - W80 Valencia | 11/20 15:20 | 54 | [235] Nika Radisic v Diletta Cherubini [456] | 1-6,0-6 | |
| ITF - W80 Madrid | 11/18 09:30 | 26 | [159] Marina B Ribera v Diletta Cherubini [456] | 3-6,6-2,6-3 | |
| ITF - W80 Madrid | 11/17 08:00 | 25 | [456] Diletta Cherubini v Kristina Mladenovic [112] | 6-3,6-4 | |
| ITF - W80 Madrid | 11/15 10:25 | 19 | [343] Angelica Moratelli v Diletta Cherubini [456] | 3-6,0-6 | |
| ITF - W80 Madrid | 11/14 12:55 | 54 | [235] Nika Radisic v Diletta Cherubini [456] | 3-6,2-6 | |
| ITF - W25 Loughborough | 10/25 13:15 | 25 | [460] Diletta Cherubini v Nefisa Berberovic [222] | 4-6,2-6 | |
| ITF - W25 Seville | 10/18 08:00 | 25 | [171] Joanne Zuger v Diletta Cherubini [457] | 3-6,6-3,7-5 | |
| ITF - W25 Santa Margherita | 10/04 11:00 | 54 | Diletta Cherubini v Tatiana Pieri | 6-7,3-6 | |
| ITF - W25 Santa Margherita | 09/21 11:00 | 25 | Diletta Cherubini v Stefania Rubini | 4-6,2-6 | |
| ITF - W25 Santa Margherita | 09/17 11:55 | 28 | [497] Jessica Pieri v Diletta Cherubini [500] | 7-5,6-4 | |
| ITF - W25 Santa Margherita | 09/16 12:00 | 27 | Diletta Cherubini v Angelica Raggi | 6-3,3-6,7-6 | |
| ITF - W25 Santa Margherita | 09/15 11:50 | 26 | [293] Darja Semenistaja v Diletta Cherubini [500] | 5-7,6-7 |