Jan Siemerink defeated Andre Agassi 6-3 3-6 6-3 in the New Haven round of 32 on hard. The upset overturned the form book — Andre Agassi came in leading the head-to-head 5–0, defending last year's semi-final. Jan Siemerink claimed a first win over Andre Agassi in six meetings, narrowing the head-to-head to 5–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-04 | Basel | R32 | hard | Andre Agassi | 6-3 6-4 |
| 1998-01-05 | Adelaide | R16 | hard | Andre Agassi | 6-4 6-3 |
| 1997-04-04 | Davis Cup WG QF: USA vs NED | RR | hard | Andre Agassi | 3-6 3-6 6-3 6-3 6-3 |
| 1996-08-26 | US Open | R32 | hard | Andre Agassi | 6-4 6-2 7-6(7) |
| 1992-08-31 | US Open | R32 | hard | Andre Agassi | 6-2 6-3 6-3 |
Averages over each player's completed matches in the selected window (199 vs 200). ATP, WTA & Challenger.
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About