Chris Woodruff defeated Pete Sampras 7-6 6-2 in the Memphis round of 32 on hard. The upset overturned the form book — Pete Sampras came in leading the head-to-head 4–0. Chris Woodruff claimed a first win over Pete Sampras in five meetings, narrowing the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-07-23 | Los Angeles | R32 | hard | Pete Sampras | 7-5 6-2 |
| 2000-05-15 | Hamburg Masters | R64 | clay | Pete Sampras | 6-4 7-6(5) |
| 2000-01-17 | Australian Open | QF | hard | Pete Sampras | 7-5 6-3 6-3 |
| 1997-02-10 | San Jose | QF | hard | Pete Sampras | 6-2 6-3 |
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 (28 vs 92). ATP, WTA & Challenger.