Justin Gimelstob defeated Chris Woodruff 6-4 7-6 in the San Jose round of 16 on hard. The upset overturned the form book — Chris Woodruff came in leading the head-to-head 3–0. Justin Gimelstob claimed a first win over Chris Woodruff in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-01-08 | Sydney | Q16 | hard | Chris Woodruff | 6-4 6-1 |
| 1997-08-11 | Indianapolis | R64 | hard | Chris Woodruff | 3-6 6-4 6-1 |
| 1997-03-10 | Indian Wells Masters | R64 | hard | Chris Woodruff | 6-4 6-7 6-3 |
Averages over each player's completed matches in the selected window (194 vs 108). 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