Jim Courier defeated Mikael Tillstrom 6-4 2-6 7-6 in the Singapore round of 16 on hard. The result followed the form book — Jim Courier came in leading the head-to-head 2–0, defending last year's quarter-final. Jim Courier extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-04-26 | Atlanta | R32 | hard | Jim Courier | 6-3 6-4 |
| 1999-04-19 | Orlando | R32 | clay | Jim Courier | 6-4 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 (96 vs 106). ATP, WTA & Challenger.