Chris Woodruff defeated Justin Gimelstob 3-6 6-4 6-1 in the Indianapolis round of 64 on hard. Chris Woodruff extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-02-08 | San Jose | R16 | hard | Justin Gimelstob | 6-4 7-6(3) |
| 1997-03-10 | Indian Wells Masters | R64 | hard | Chris Woodruff | 6-4 6-7(7) 6-3 |
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.