Doroteja Joksovic defeated Kristina Milenkovic 6-7 7-6 10-6 in the W15 Prokuplje 2 q16 on clay. The upset overturned the form book — Kristina Milenkovic came in leading the head-to-head 1–0. Doroteja Joksovic claimed a first win over Kristina Milenkovic in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2021-06-27 | W15 Prokuplje 1 | Q64 | clay | Kristina Milenkovic | 6-2 3-0 |