Jan Michael Gambill defeated Fabrice Santoro 7-6 6-1 in the Nottingham round of 16 on grass. The upset overturned the form book — Fabrice Santoro came in leading the head-to-head 2–1, defending last year's quarter-final. Jan Michael Gambill narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-06-26 | Wimbledon | R64 | grass | Jan Michael Gambill | 4-6 6-4 6-2 6-2 |
| 1999-08-30 | US Open | R64 | hard | Fabrice Santoro | 6-4 6-2 3-6 6-7(7) 4-4 RET |
| 1999-03-15 | Miami Masters | R64 | hard | Fabrice Santoro | 7-5 6-2 |
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.