Kristina Milenkovic advanced when Doroteja Joksovic retired 6-2 3-0 in the W15 Prokuplje 1 q64. Kristina Milenkovic claimed a first win over Doroteja Joksovic in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-07-09 | W15 Prokuplje 2 | Q16 | clay | Doroteja Joksovic | 6-7(4) 7-6(3) 10-6 |