Jan Michael Gambill defeated Franco Squillari 3-6 6-3 6-4 in the Scottsdale round of 32 on hard. The result followed the form book — Jan Michael Gambill came in leading the head-to-head 1–0, defending last year's quarter-final. Jan Michael Gambill extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-21 | Wimbledon | R128 | grass | Jan Michael Gambill | 6-1 6-3 7-6(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 200). ATP, WTA & Challenger.