Ignacio Hirigoyen defeated Eric Drew 4-6 6-2 6-2 in the USA F22A qualifying round on clay. The upset overturned the form book — Eric Drew came in leading the head-to-head 2–1. Ignacio Hirigoyen narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-12-06 | USA F22 | R64 | hard | Ignacio Hirigoyen | 6-3 3-6 6-0 |
| 1999-09-10 | USA 2 Masters 1 | R32 | hard | Eric Drew | 6-4 7-6 |
| 1999-07-05 | USA F10 | R32 | hard | Eric Drew | 6-1 3-6 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.