Frederick Sundsten defeated Yordan Kanev 4-6 6-2 6-4 in the Canada F3 round of 16 on hard. The upset overturned the form book — Yordan Kanev came in leading the head-to-head 1–0. Frederick Sundsten claimed a first win over Yordan Kanev in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-10-31 | Canada F1 | R32 | hard | Yordan Kanev | 6-0 6-2 |