Jim Courier defeated Mikael Tillstrom 6-4 7-5 in the Orlando round of 32 on clay. The result followed the form book — Jim Courier came in leading the head-to-head 2–0, defending the title. 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 |
| 1998-10-12 | Singapore | R16 | hard | Jim Courier | 6-4 2-6 7-6(3) |
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 (57 vs 65). ATP, WTA & Challenger.