Gorka Fraile advanced when Sergi Duran retired 6-3 1-0 in the Spain 3 Masters 1 qualifying round. Gorka Fraile claimed a first win over Sergi Duran in six meetings, narrowing the head-to-head to 5–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-01-29 | Spain 2 Masters 4 | R32 | clay | Sergi Duran | 2-6 6-3 6-3 |
| 1999-01-02 | Spain 1 Masters 4 | R32 | clay | Sergi Duran | 6-7 6-1 6-4 |
| 1998-05-08 | Spain 5 Masters 3 | F | clay | Sergi Duran | 6-1 5-7 6-3 |
| 1998-02-27 | Spain 3 Masters 3 | R16 | clay | Sergi Duran | 6-4 7-5 |
| 1997-10-17 | Spain 9 Masters 1 | SF | clay | Sergi Duran | 6-1 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.