Mark Philippoussis defeated Jason Stoltenberg 5-7 6-1 6-3 6-3 in the Wimbledon round of 16 on grass. The upset overturned the form book — Jason Stoltenberg came in leading the head-to-head 1–0, defending last year's round of 32. Mark Philippoussis claimed a first win over Jason Stoltenberg in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-24 | Roland Garros | R128 | clay | Jason Stoltenberg | 7-6(4) 6-4 6-1 |
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 138). ATP, WTA & Challenger.