David Critchley defeated Rafael De Mesa 6-4 2-6 6-4 in the USA F20 round of 32 on hard. The upset overturned the form book — Rafael De Mesa came in leading the head-to-head 1–0. David Critchley claimed a first win over Rafael De Mesa in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-17 | USA F4 | R32 | clay | Rafael De Mesa | 6-0 6-0 |