Naima Karamoko defeated Kristina Milenkovic 6-3 6-2 in the W15 Monastir 31 round of 32 on hard. The upset overturned the form book — Kristina Milenkovic came in leading the head-to-head 1–0. Naima Karamoko claimed a first win over Kristina Milenkovic in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2021-08-22 | W25 Verbier | Q32 | clay | Kristina Milenkovic | 7-6(5) 7-5 |