Jan Weinzierl defeated David Caballero 7-5 6-0 in the Germany F7 round of 16 on clay. Jan Weinzierl extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-11-27 | Spain F16 | R32 | clay | Jan Weinzierl | 6-1 5-2 |
| 1998-01-30 | Spain 2 Masters 2 | R16 | clay | David Caballero | 6-0 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.