Chris Woodruff defeated Tim Henman 6-1 1-6 7-5 in the Indian Wells Masters quarter-final on hard. Chris Woodruff extended 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 |
| 1999-06-21 | Wimbledon | R64 | grass | Tim Henman | 6-4 6-3 7-6(4) |
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 (108 vs 200). ATP, WTA & Challenger.