Lester Cook defeated Jesse Witten 2-6 7-6 6-0 in the USA F6 qualifying round on hard. The upset overturned the form book — Jesse Witten came in leading the head-to-head 3–0. Lester Cook claimed a first win over Jesse Witten in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-06-08 | USA F12 | QF | hard | Jesse Witten | 7-5 6-1 |
| 2009-03-30 | USA F7 | QF | hard | Jesse Witten | 6-4 4-6 7-6(6) |
| 2006-01-16 | USA F2 | R32 | hard | Jesse Witten | 6-4 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.