Lester Cook defeated Ryler Deheart 7-6 4-6 6-2 in the USA F6 qualifying round on hard. The upset overturned the form book — Ryler Deheart came in leading the head-to-head 2–0. Lester Cook claimed a first win over Ryler Deheart in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-06-09 | USA F12 | QF | hard | Ryler Deheart | 6-2 6-4 |
| 2007-03-19 | Canada F3 | QF | hard | Ryler Deheart | 6-4 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.