Chris Woodruff defeated Tim Henman 7-5 1-6 6-4 3-6 7-5 in the Australian Open round of 16 on hard. The upset overturned the form book — Tim Henman came in defending last year's round of 32. Chris Woodruff extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-21 | Wimbledon | R64 | grass | Tim Henman | 6-4 6-3 7-6(4) |
| 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 (68 vs 200). ATP, WTA & Challenger.