Michael Mcclune advanced when Lester Cook retired 6-4 4-1 in the USA F29 round of 32. Michael Mcclune claimed a first win over Lester Cook in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-03-30 | USA F7 | R32 | hard | Lester Cook | 6-7(5) 7-6(1) 6-3 |
| 2006-09-25 | USA F24 | R32 | hard | Lester Cook | 7-6(4) 7-5 |
| 2005-09-12 | USA F22 | R32 | hard | Lester Cook | 6-1 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.