Wayne Black defeated Tim Henman 6-3 6-4 in the Indian Wells Masters round of 64 on hard. The upset overturned the form book — Tim Henman came in leading the head-to-head 1–0, but Wayne Black had been the form player, winning 3 of their last 4 on hard. Wayne Black claimed a first win over Tim Henman in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-02-08 | Dubai | R32 | hard | Tim Henman | 6-0 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 (100 vs 200). ATP, WTA & Challenger.