Rodolfo Rake defeated Charles Edouard Maria 7-6 7-6 in the Denmark F2 round of 32 on clay. The upset overturned the form book — Charles Edouard Maria came in leading the head-to-head 1–0. Rodolfo Rake claimed a first win over Charles Edouard Maria in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-01-23 | Central America Masters 3 | R32 | clay | Charles Edouard Maria | 6-2 6-4 |