Ramon Delgado defeated Pete Sampras 7-6 6-3 6-4 in the Roland Garros round of 64 on clay. The upset overturned the form book — Pete Sampras came in leading the head-to-head 2–0, defending last year's round of 32. Ramon Delgado claimed a first win over Pete Sampras in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-03-01 | Scottsdale | R32 | hard | Pete Sampras | 7-6(2) 6-2 |
| 1998-04-27 | Atlanta | QF | hard | Pete Sampras | 7-6(6) 7-6(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 (154 vs 200). ATP, WTA & Challenger.