Kentaro Masuda defeated Julien Jeanpierre 4-6 6-3 7-5 in the Spain F4 round of 32 on clay. The upset overturned the form book — Julien Jeanpierre came in leading the head-to-head 1–0. Kentaro Masuda claimed a first win over Julien Jeanpierre in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-04 | Spain 6 Masters 3 | R32 | clay | Julien Jeanpierre | 6-1 6-7 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.