Jonathan Chu defeated Alex Clayton 6-4 6-4 in the USA F19 round of 16 on hard. The upset overturned the form book — Alex Clayton came in leading the head-to-head 1–0. Jonathan Chu claimed a first win over Alex Clayton in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-06-26 | USA F15 | R16 | clay | Alex Clayton | 6-4 7-5 |