Chris Woodruff defeated Thomas Enqvist 6-4 6-4 in the Indian Wells Masters round of 32 on hard. Chris Woodruff extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-08-28 | US Open | R64 | hard | Thomas Enqvist | 6-3 6-2 6-2 |
| 1999-08-09 | Cincinnati Masters | R32 | hard | Chris Woodruff | 6-1 7-5 |
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 (163 vs 200). ATP, WTA & Challenger.