Maaike Koutstaal defeated Tamara Aranda Nunez 3-6 7-5 6-2 in the Madrid 10K round of 32 on clay. The upset overturned the form book — Tamara Aranda Nunez came in leading the head-to-head 2–0. Maaike Koutstaal claimed a first win over Tamara Aranda Nunez in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-07-12 | Getxo 25K | R32 | clay | Tamara Aranda Nunez | 6-3 3-6 6-4 |
| 1999-03-29 | Pontevedra 10K | R32 | hard | Tamara Aranda Nunez | 2-6 6-4 7-6 |