Chris Woodruff defeated Andre Agassi 4-6 6-4 6-7 6-3 6-2 in the Roland Garros round of 64 on clay. The upset overturned the form book — Andre Agassi came in leading the head-to-head 1–0, defending last year's quarter-final. Chris Woodruff claimed a first win over Andre Agassi in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-24 | Roland Garros | R32 | clay | Andre Agassi | 6-4 6-4 6-3 |
Averages over each player's completed matches in the selected window (164 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