Chris Woodruff defeated Justin Gimelstob 3-6 6-4 6-1 in the Indianapolis round of 64 on hard. The result followed the form book — Chris Woodruff came in leading the head-to-head 2–1, defending last year's round of 16. Chris Woodruff extended 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 |
| 1999-02-08 | San Jose | R16 | hard | Justin Gimelstob | 6-4 7-6 |
| 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 (163 vs 200). 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