| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-04-26 | Atlanta | R32 | hard | Mark Woodforde | 2-6 6-3 6-4 |
| 1999-03-15 | Miami Masters | R128 | hard | Lleyton Hewitt | 6-2 6-1 |
| 1999-03-08 | Indian Wells Masters | R64 | hard | Lleyton Hewitt | 4-6 6-2 6-4 |
| 1999-03-01 | Scottsdale | SF | hard | Lleyton Hewitt | 6-2 6-2 |
| 1998-01-05 | Adelaide | R16 | hard | Lleyton Hewitt | 4-6 7-6(1) 6-1 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.