Stadium: Clay 5 Round: 62 Ground: Hardcourt outdoor
| ITF Women Heraklion | 2018/11/03 10:00 | Savescu, Iulia v Milenkovic, Dejana | 7-5,5-7,3-6 |
| ITF Women Heraklion | 2018/10/27 07:00 | Milenkovic, Dejana v Gloria Ceschi | 3-6,1-6 |
| Cairo, Singles W-WITF-EGY-02A | 2018/09/26 11:15 | Viktoria Morvayova v Milenkovic, Dejana | 6-0,6-3 |
| Cairo, Singles W-WITF-EGY-02A | 2018/09/19 14:45 | Anna Ureke v Milenkovic, Dejana | 6-0,6-1 |
| Cairo, Singles W-WITF-EGY-02A | 2018/09/11 07:30 | Kakuya, Akiho v Milenkovic, Dejana | 6-3,6-2 |
| ITF Women Vrnjacka Banja | 2018/08/19 10:00 | Milenkovic, Dejana v Gal, Anja | 0-6,3-6 |
| ITF Women Arad Qual | 2018/08/05 08:00 | Jana Bojovic v Milenkovic, Dejana | 6-0,6-2 |
| ITF Women Arad Qual | 2018/08/04 10:00 | Milenkovic, Dejana v Popescu, Maria Alexandra Medeea | 6-1,6-1 |
| ITF Women Heraklion | 2018/11/03 08:00 | Ani Vangelova v Kuhlman, Josie | 7-5,7-5 |
| ITF Women Heraklion | 2018/11/02 10:00 | Kuhlman, Josie v Mchedlidze, Elene | 6-4,6-4 |
| ITF Women Heraklion | 2018/11/01 10:15 | Kuhlman, Josie v Novac, Izabela Gabriela | 6-1,6-1 |
| ITF Women Florence | 2018/10/15 15:30 | Turati, Bianca v Kuhlman, Josie | 6-4,6-2 |
| ITF Women Charleston | 2018/10/01 16:00 | Kuhlman, Josie v Alana Smith | 3-6,2-6 |
| ITF Women Charleston | 2018/09/30 13:00 | Kuhlman, Josie v Baranovski, Anna | 7-5,6-1 |
| Daytona Beach, Singles Qualifying W-WITF-USA-01A | 2018/01/08 19:30 | Kuhlman, Josie v Anna Danilina | 2-6,1-6 |
| Daytona Beach, Singles Qualifying W-WITF-USA-01A | 2018/01/07 18:00 | Robin Anderson v Kuhlman, Josie | 6-1,3-6,2-6 |