Ryler Deheart defeated Lester Cook 6-4 6-4 in the Canada F3 qualifying round on hard. Ryler Deheart extended 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 |
| 2008-03-03 | USA F6 | QF | hard | Lester Cook | 7-6(4) 4-6 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.