Tim Smyczek advanced when Lester Cook retired 4-1 in the USA F23 qualifying round. Tim Smyczek extended the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-03-03 | USA F6 | SF | hard | Tim Smyczek | 6-3 4-6 6-4 |
| 2007-09-24 | USA F24 | R16 | hard | Tim Smyczek | 6-2 2-6 6-4 |
| 2007-04-16 | USA F8 | R32 | hard | Tim Smyczek | 6-0 1-0 |
| 2007-02-26 | USA F5 | R16 | hard | Lester Cook | 7-6(4) 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.