Tim Henman defeated Chris Woodruff 6-4 6-3 7-6 in the Wimbledon round of 64 on grass. The upset overturned the form book — Chris Woodruff came in leading the head-to-head 2–0. Tim Henman claimed a first win over Chris Woodruff in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-01-17 | Australian Open | R16 | hard | Chris Woodruff | 7-5 1-6 6-4 3-6 7-5 |
| 1999-03-08 | Indian Wells Masters | QF | hard | Chris Woodruff | 6-1 1-6 7-5 |
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.