| UTR Pro Skopje Women | 06/28 13:15 | 28 | Nina Zabrdac v Elena Milutinovic | Retired | |
| UTR Pro Skopje Women | 06/27 06:00 | - | Julia Terziyska v Elena Milutinovic | 6-0,6-0 | |
| UTR Pro Skopje Women | 06/26 08:15 | - | Lara Stojanovski v Elena Milutinovic | 6-4,6-0 | |
| UTR Pro Skopje Women | 06/25 11:45 | - | Alexia Patru v Elena Milutinovic | 6-4,6-4 | |
| UTR Pro Skopje Women | 06/23 07:00 | - | Bojana Marinkovic v Elena Milutinovic | 6-1,6-0 | |
| ITF W15 Kursumlijska Banja | 06/18 07:00 | - | Petra Konjikusic v Elena Milutinovic | 6-0,6-1 | |
| UTR Pro Pazardzhik Women | 05/25 13:40 | 29 | Elena Milutinovic v Rianna Coreisa | Walkover | |
| UTR Pro Pazardzhik Women | 05/24 13:45 | 28 | Gebriela Mihaylova v Elena Milutinovic | Retired | |
| UTR Pro Pazardzhik Women | 05/23 06:00 | - | Aleksandra Rangelova v Elena Milutinovic | 6-3,6-2 | |
| UTR Pro Pazardzhik Women | 05/22 11:00 | - | Victoria Lazarova v Elena Milutinovic | 0-6,5-7 | |
| UTR Pro Pazardzhik Women | 05/20 13:35 | - | Andzhelina Kostova v Elena Milutinovic | 6-2,7-5 | |
| UTR Pro Pazardzhik Women | 05/20 06:00 | - | Julia Terziyska v Elena Milutinovic | CANC |