Gustavo Kuerten defeated Pete Sampras 6-7 6-3 6-4 in the Masters Cup semi-final on hard. The upset overturned the form book — Pete Sampras came in leading the head-to-head 2–0. Gustavo Kuerten claimed a first win over Pete Sampras in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-03-20 | Miami Masters | F | hard | Pete Sampras | 6-1 6-7(2) 7-6(5) 7-6(8) |
| 1999-11-22 | Tour Finals | RR | hard | Pete Sampras | 6-2 6-3 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.