By surface
| Surface | Chris Woodruff | Justin Gimelstob |
|---|---|---|
| Hard | 2 | 1 |
All meetings (3)
| Date | Tour | Tournament | Round | Surface | Winner | Set 1 | Set 2 | Set 3 | Set 4 | Set 5 |
|---|---|---|---|---|---|---|---|---|---|---|
| 1999-02-08 | ATP | San Jose | Round of 16 | Hard | Justin Gimelstob | 4-6 | 6-73 | |||
| 1997-08-11 | ATP | Indianapolis | Round of 64 | Hard | Chris Woodruff | 3-6 | 6-4 | 6-1 | ||
| 1997-03-10 | ATP | Indian Wells Masters | Round of 64 | Hard | Chris Woodruff | 6-4 | 6-77 | 6-3 |