Luis Herrera defeated Gilad Bloom 7-5 6-1 in the New Haven round of 64 on hard. The upset overturned the form book — Gilad Bloom came in leading the head-to-head 1–0, defending last year's round of 32. Luis Herrera claimed a first win over Gilad Bloom in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1990-07-16 | Washington | R64 | hard | Gilad Bloom | 6-4 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.