Carlos Moya defeated Gustavo Kuerten 7-6 6-1 in the Buenos Aires semi-final on clay. The upset overturned the form book — Gustavo Kuerten came in leading the head-to-head 4–2, defending last year's round of 32. Carlos Moya narrowed the head-to-head to 4–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-03 | Hamburg Masters | QF | clay | Carlos Moya | 6-0 6-2 |
| 1999-04-02 | Davis Cup WG R1: ESP vs BRA | RR | clay | Gustavo Kuerten | 6-2 6-4 6-1 |
| 1999-03-08 | Indian Wells Masters | SF | hard | Carlos Moya | 6-3 1-6 6-1 |
| 1998-09-28 | Mallorca | F | grass | Gustavo Kuerten | 6-7(5) 6-2 6-3 |
| 1998-07-20 | Stuttgart Outdoor | SF | clay | Gustavo Kuerten | 7-6(6) 6-4 |
| 1998-04-03 | Davis Cup WG R1: BRA vs ESP | RR | clay | Gustavo Kuerten | 5-7 1-6 6-4 6-4 6-4 |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Averages over each player's completed matches in the selected window (200 vs 115). ATP, WTA & Challenger.