Lleyton Hewitt defeated Mark Woodforde 6-3 2-6 6-1 in the Adelaide round of 32 on hard. The result followed the form book — Lleyton Hewitt came in leading the head-to-head 4–1, defending last year's final. Lleyton Hewitt extended the head-to-head to 5–1.
| 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 |
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 9). ATP, WTA & Challenger.