Miguel Angel Lopez Jaen defeated Carlos Castellanos 6-2 6-2 in the Spain 3 3 round of 32 on clay. The upset overturned the form book — Carlos Castellanos came in leading the head-to-head 1–0. Miguel Angel Lopez Jaen claimed a first win over Carlos Castellanos in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-23 | Spain F7 | R32 | clay | Carlos Castellanos | 3-6 6-4 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.