| ITF - Antalya W15 | 02/18 11:00 | 26 | Martina Caregaro v Sohyun Park | 7-5,3-6,1-6 | |
| ITF - Antalya W15 | 02/16 08:00 | 25 | Martina Caregaro v Antonia Samudio | 7-6,2-6,7-6 | |
| ITF - Andrezieux-Boutheon W60 | 01/25 11:05 | 54 | Martina Caregaro v Maryna Zanevska | 2-6,4-6 | |
| ITF - Hamburg W25 | 01/14 14:10 | 26 | [305] Martina Caregaro v Qinwen Zheng [287] | 2-6,0-6 | |
| ITF - Hamburg W25 | 01/12 10:00 | 25 | [256] Tena Lukas v Martina Caregaro [305] | 5-7,6-7 | |
| WTA Abu Dhabi | 01/06 09:05 | 19 | [318] Bianca Turati v Martina Caregaro [305] | 6-0,6-3 | |
| WTA Abu Dhabi | 01/05 12:45 | 64 | [387] Valeriya Strakhova v Martina Caregaro [305] | 3-6,3-6 | |
| ITF - Selva Gardena W25 | 12/15 08:00 | 25 | [302] Martina Caregaro v Indy De Vroome [197] | 6-4,4-6,6-7 | |
| ITF - Grado W25 | 09/16 14:35 | 25 | Malene Helgo v Martina Caregaro | 6-3,6-4 | |
| ITF - Tarvisio W25 | 09/09 08:30 | 25 | [293] Martina Caregaro v Lea Boskovic [305] | 1-6,3-6 | |
| ITF - Cordenons W15 | 08/27 11:30 | 27 | [293] Martina Caregaro v Federica Di Sarra [441] | 1-6,2-6 | |
| ITF - Cordenons W15 | 08/26 08:30 | 26 | Martina Caregaro v Vanda Lukacs | 6-4,6-2 | |
| ITF - Cordenons W15 | 08/25 07:55 | 25 | Martina Caregaro v Giulia Martinelli | 6-3,6-3 | |
| Włochy - National Tour - Kobiety | 07/01 16:35 | 1 | [292] Martina Caregaro v Lucia Bronzetti [331] | 2-6,2-6 | |
| Włochy - Umbrian Open - Kobiety | 06/24 08:00 | 1 | [292] Martina Caregaro v Camilla Rosatello [443] | 6-3,4-6,10-12 | |
| ITF - Potchefstroom W25 | 03/11 07:00 | 25 | [292] Martina Caregaro v Laura Pigossi [423] | 7-5,4-6,2-6 | |
| ITF - Potchefstroom W25 | 03/05 07:30 | 26 | Joanne Zuger v Martina Caregaro | 5-7,7-6,6-4 | |
| ITF - Potchefstroom W25 | 03/04 07:00 | 25 | [354] Fanni Stollar v Martina Caregaro [289] | 6-7,7-5,3-6 | |
| ITF - Macon W25 | 02/26 10:00 | 25 | [294] Martina Caregaro v Vera Lapko [378] | 3-6,3-6 | |
| ITF - Navi Mumbai W25 | 12/21 10:30 | 28 | [147] Barbara Haas v Martina Caregaro [318] | 3-6,6-3,6-4 | |
| ITF - Navi Mumbai W25 | 12/20 10:00 | 27 | [184] Valeria Savinykh v Martina Caregaro [318] | 3-6,6-7 | |
| ITF - Navi Mumbai W25 | 12/19 10:45 | 26 | [369] Valeriya Strakhova v Martina Caregaro [318] | 4-6,1-6 | |
| ITF - Navi Mumbai W25 | 12/18 14:35 | 25 | [163] Ji-Hee Choi v Martina Caregaro [318] | 2-6,1-6 | |
| ITF - Pune W25 | 12/12 05:30 | 26 | [309] Peangtarn Plipuech v Martina Caregaro [317] | 7-6,6-2 | |
| ITF - Pune W25 | 12/11 07:30 | 25 | Martina Caregaro v Niditra Rajmohan | 6-0,6-2 | |
| ITF - Solarino W25 | 11/27 09:55 | 25 | [319] Tayisiya Morderger v Martina Caregaro [319] | 6-2,6-1 | |
| ITF - Solarino W25 | 11/20 11:50 | 25 | [423] Olga Saez Larra v Martina Caregaro [318] | 7-5,6-4 | |
| ITF - Hua Hin W25 | 11/13 08:05 | 25 | Martina Caregaro v Hurricane Tyra Black | 4-6,4-6 | |
| ITF - Hua Hin W25 | 11/06 06:05 | 25 | Kyoka Okamura v Martina Caregaro | 1-6,7-6,6-2 | |
| ITF - Hua Hin W25 | 11/06 03:00 | - | [258] Kyoka Okamura v Martina Caregaro [311] | 1-6,7-6,6-2 |