Germana Di Natale defeated Karen Cross 6-4 6-1 in the Dinan 25K round of 32 on clay. The upset overturned the form book — Karen Cross came in leading the head-to-head 2–0. Germana Di Natale claimed a first win over Karen Cross in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-04-12 | Cagnes sur Mer 25K | R16 | hard | Karen Cross | 6-2 6-4 |
| 1999-02-15 | Redbridge 25K | R32 | hard | Karen Cross | 6-2 6-3 |