Massimo Ocera defeated Marcos Jimenez Letrado 7-5 6-3 in the Spain F23 round of 16 on hard. The upset overturned the form book — Marcos Jimenez Letrado came in leading the head-to-head 1–0. Massimo Ocera claimed a first win over Marcos Jimenez Letrado in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-09-29 | Spain F25 | R16 | hard | Marcos Jimenez Letrado | 7-5 6-4 |