Thomas Enqvist defeated Chris Woodruff 6-3 6-2 6-2 in the US Open round of 64 on hard. The upset overturned the form book — Chris Woodruff came in leading the head-to-head 2–0, defending last year's round of 32. Thomas Enqvist claimed a first win over Chris Woodruff in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-09 | Cincinnati Masters | R32 | hard | Chris Woodruff | 6-1 7-5 |
| 1997-03-10 | Indian Wells Masters | R32 | hard | Chris Woodruff | 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 (200 vs 68). ATP, WTA & Challenger.