Tyler Cleveland defeated Wesley Whitehouse 7-6 7-5 in the USA F5 qualifying round on hard. The upset overturned the form book — Wesley Whitehouse came in leading the head-to-head 2–0. Tyler Cleveland claimed a first win over Wesley Whitehouse in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2007-07-28 | Washington | Q16 | hard | Wesley Whitehouse | 7-6(6) 1-6 7-6(4) |
| 2007-04-16 | USA F8 | R16 | hard | Wesley Whitehouse | 6-1 6-7(1) 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.