Alex Clayton defeated Jonathan Chu 6-4 7-5 in the USA F15 round of 16 on clay. The upset overturned the form book — Jonathan Chu came in leading the head-to-head 1–0. Alex Clayton claimed a first win over Jonathan Chu in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-07-24 | USA F19 | R16 | hard | Jonathan Chu | 6-4 6-4 |