James Blake defeated Daniel Wajnberg 6-3 6-4 in the Canada F1 qualifying round on hard. The result followed the form book — James Blake came in leading the head-to-head 1–0. James Blake extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-21 | Canada F2 | R32 | hard | James Blake | 6-2 4-6 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.