Jan Siemerink defeated Nicolas Lapentti 6-4 6-3 in the New Haven round of 64 on hard. The upset overturned the form book — Nicolas Lapentti came in leading the head-to-head 4–0, defending last year's round of 32. Jan Siemerink claimed a first win over Nicolas Lapentti in five meetings, narrowing 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 |
| 1997-08-18 | Long Island | R32 | hard | Nicolas Lapentti | 7-6(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 (153 vs 200). ATP, WTA & Challenger.