Jan Weinzierl advanced when German Puentes retired 4-1 in the France F3 round of 16. Jan Weinzierl narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-02-26 | Spain 3 Masters 2 | QF | clay | German Puentes | 7-5 6-3 |
| 1999-01-29 | Spain 2 Masters 3 | R32 | clay | German Puentes | 7-5 6-7 6-4 |
| 1999-01-02 | Spain 1 Masters 1 | SF | clay | German Puentes | 7-5 7-5 |
| 1998-02-27 | Spain 3 Masters 1 | R16 | clay | Jan Weinzierl | 6-1 1-6 6-0 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.