Antonio Prieto defeated Jeff Loehr 6-2 6-1 in the USA F1 round of 64 on hard. The upset overturned the form book — Jeff Loehr came in leading the head-to-head 1–0. Antonio Prieto claimed a first win over Jeff Loehr in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-06-01 | USA F4 | R32 | clay | Jeff Loehr | 7-6 6-1 |