Ground: Clay
| UTR Pro Thessaloniki Women | 2023/06/03 08:31 | Athina Pitta v Styliani Roussopoulou | 7-6,6-4 |
| UTR Pro Thessaloniki Women | 2023/06/02 10:00 | Isabelle Kouzmanov v Styliani Roussopoulou | 1-6,2-6 |
| UTR Pro Thessaloniki Women | 2023/06/01 06:00 | Nina Ugrelidze v Styliani Roussopoulou | 1-6,6-4,3-6 |
| UTR Pro Thessaloniki Women | 2023/05/30 07:35 | Stefana Lazar v Styliani Roussopoulou | 6-3,6-4 |
| UTR Pro Thessaloniki Women | 2023/05/29 05:00 | Styliani Roussopoulou v Anastasia Iamachkine | 1-6,2-6 |
| ITF W15 Kursumlijska Banja | 2023/05/09 08:00 | Junhan Zhang v Styliani Roussopoulou | 6-1,6-2 |
| ITF W15 Kursumlijska Banja | 2023/05/08 12:00 | Mija Ljubic v Styliani Roussopoulou | 6-2,1-6,4-10 |
| ITF W15 Kursumlijska Banja | 2023/05/01 17:25 | Styliani Roussopoulou v Anja Stankovic | 4-6,2-6 |
| ITF W15 Antalya | 2023/05/16 10:25 | Eleanor Baglow v Andrea Obradovic | 6-7,2-6 |
| ITF W15 Antalya | 2023/05/12 08:25 | Natalia Siedliska v Andrea Obradovic | 6-1,6-1 |
| ITF W15 Antalya | 2023/05/11 07:30 | Andrea Obradovic v Anastasia Kovaleva | 6-4,6-3 |
| ITF W15 Antalya | 2023/05/09 09:50 | Melis Ayda Uyar v Andrea Obradovic | 2-6,1-6 |
| ITF W60 Koper | 2023/04/16 08:00 | Andrea Obradovic v Angelina Wirges | 6-7,2-6 |
| ITF W15 Antalya | 2023/03/31 10:10 | Andrea Obradovic v Basak Eraydin | 2-6,2-6 |
| ITF W15 Antalya | 2023/03/30 10:00 | Andrea Obradovic v Ilay Yoruk | 7-6,6-0 |
| ITF W15 Antalya | 2023/03/29 09:25 | Eva Garkusha v Andrea Obradovic | 6-2,2-6,2-6 |