Lars Zimmermann defeated Jalal Chafai 6-3 6-1 in the USA F1 round of 64 on hard. The upset overturned the form book — Jalal Chafai came in leading the head-to-head 1–0. Lars Zimmermann claimed a first win over Jalal Chafai in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-06-12 | Netherlands 3 | R32 | clay | Jalal Chafai | 6-2 6-4 |