Nicolas Lapentti defeated Jan Siemerink 7-6 6-4 in the Long Island round of 32 on hard. The result followed the form book — Nicolas Lapentti came in leading the head-to-head 3–1. Nicolas Lapentti extended the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-18 | Lyon | R32 | clay | Nicolas Lapentti | 3-6 6-3 7-6(4) |
| 1999-09-24 | Davis Cup WG PO: ECU vs NED | RR | clay | Nicolas Lapentti | 6-4 4-6 6-3 6-2 |
| 1999-08-16 | Indianapolis | SF | hard | Nicolas Lapentti | 6-4 6-2 |
| 1998-08-17 | New Haven | R64 | hard | Jan Siemerink | 6-4 6-3 |
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 199). ATP, WTA & Challenger.