Tim Henman defeated Mariano Puerta 6-1 6-2 in the Cincinnati Masters round of 32 on hard. The result followed the form book — Tim Henman came in leading the head-to-head 2–0, defending last year's quarter-final. Tim Henman extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-03 | Hamburg Masters | R16 | clay | Tim Henman | 6-4 6-1 |
| 1999-04-12 | Barcelona | R32 | clay | Tim Henman | 7-6(1) 6-7(3) 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 161). ATP, WTA & Challenger.