Rafael De Mesa defeated David Critchley 6-0 6-0 in the USA F4 round of 32 on clay. The upset overturned the form book — David Critchley came in leading the head-to-head 1–0, but Rafael De Mesa had been the form player, winning 3 of their last 5 on clay. Rafael De Mesa claimed a first win over David Critchley in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-22 | USA F20 | R32 | hard | David Critchley | 6-4 2-6 6-4 |