Karen Cross defeated Germana Di Natale 6-2 6-3 in the Redbridge 25K round of 32 on hard. Karen Cross extended 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 |
| 1999-03-22 | Dinan 25K | R32 | clay | Germana Di Natale | 6-4 6-1 |