Stadium: Court 5 Round: 26 Ground: Clay
| ITF Women Horb Qual | 2017/07/23 22:00 | Sina Herrmann v Grimm, Chiara | 3-6,0-6 |
| ITF - W15 Antalya | 2019/04/24 12:50 | Bojana Marinkovic v Grimm, Chiara | 4-6,2-6 |
| ITF - W15 Antalya | 2019/04/23 07:00 | Sapfo Sakellaridi v Grimm, Chiara | 3-6,1-6 |
| ITF - W15 Antalya | 2019/04/22 07:00 | Nicolini, Sofia Haydee v Grimm, Chiara | 2-6,1-6 |
| Tabarka, Singles W-ITF-TUN-18A | 2019/03/11 12:30 | Schultheiss, Carmen v Grimm, Chiara | 3-6,6-7 |
| Tabarka, Singles W-ITF-TUN-18A | 2019/03/11 08:00 | Grimm, Chiara v Almudena S-L Fernandez | 3-6,6-4,10-7 |
| ITF - W15 Antalya | 2019/01/16 10:55 | Grimm, Chiara v Naho Sato | 3-6,4-6 |
| ITF - W15 Antalya | 2019/01/14 07:00 | Grimm, Chiara v Abdioglu, Aylin | 6-0,6-0 |
| Antalya, Singles Qualifying W-WITF-TUR-08A | 2018/12/20 10:05 | Gaspar-Ivan, Ioana v Grimm, Chiara | 6-1,6-4 |
| ITF - W15 Antalya | 2019/04/24 11:45 | Pepelyaeva, Veronika v Sina Herrmann | 2-6,6-0,3-6 |
| ITF - W15 Antalya | 2019/04/23 07:00 | Tarasova, Ksenia v Sina Herrmann | 1-6,4-6 |
| ITF - W15 Antalya | 2019/04/15 07:00 | Sina Herrmann v Kubanova, Karolina | 2-6,5-7 |
| ITF - W15 Antalya | 2019/03/07 09:30 | Sina Herrmann v Molinaro, Eleonora | 2-6,3-6 |
| ITF - W15 Antalya | 2019/03/05 09:30 | Sapfo Sakellaridi v Sina Herrmann | 6-3,4-6,3-6 |
| ITF Women Badenweiler | 2018/09/04 10:40 | Schultheiss, Carmen v Sina Herrmann | 4-6,6-3,6-1 |
| ITF Women Rotterdam | 2018/08/20 10:00 | Eva Vedder v Sina Herrmann | 6-4,6-2 |
| ITF Women Rotterdam | 2018/08/19 07:00 | Sina Herrmann v Versteeg, Kelly | 2-6,7-5,6-4 |