Yevgeny Kafelnikov defeated Chris Woodruff 7-6 5-7 6-4 in the Rome Masters round of 64 on clay. The result followed the form book — Yevgeny Kafelnikov came in leading the head-to-head 4–1, defending last year's round of 16. Yevgeny Kafelnikov extended the head-to-head to 5–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-01-15 | Australian Open | R32 | hard | Yevgeny Kafelnikov | 6-7(3) 7-5 6-2 6-3 |
| 2000-08-07 | Cincinnati Masters | R32 | hard | Yevgeny Kafelnikov | 6-4 7-6(3) |
| 1999-08-09 | Cincinnati Masters | R16 | hard | Yevgeny Kafelnikov | 6-4 6-4 |
| 1997-08-04 | Cincinnati Masters | R32 | hard | Yevgeny Kafelnikov | 7-6(3) 7-6(6) |
| 1997-07-28 | Canada Masters | SF | hard | Chris Woodruff | 5-7 7-5 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 (200 vs 108). ATP, WTA & Challenger.