Luke Smith defeated Todor Enev 6-3 6-1 in the Australia F5 round of 32 on grass. The upset overturned the form book — Todor Enev came in leading the head-to-head 1–0. Luke Smith claimed a first win over Todor Enev in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-11-26 | Australia F6 | QF | grass | Todor Enev | 6-2 6-2 |