Ricardo Schlachter defeated Walter Grinovero 1-6 7-5 6-4 in the Uruguay F2 round of 16 on clay. The upset overturned the form book — Walter Grinovero came in leading the head-to-head 1–0. Ricardo Schlachter claimed a first win over Walter Grinovero in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-07-19 | Uruguay F1 | F | clay | Walter Grinovero | 6-1 6-3 |