Carlos Castellanos defeated Pablo Garcia Gaitan 6-3 6-3 in the Spain F5 round of 16 on clay. The upset overturned the form book — Pablo Garcia Gaitan came in leading the head-to-head 1–0. Carlos Castellanos claimed a first win over Pablo Garcia Gaitan in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-05-22 | Morocco F3 | R16 | clay | Pablo Garcia Gaitan | 6-4 |