Johan Kareld defeated Thomas Blake 6-3 6-4 in the Jamaica F3 round of 16 on hard. The upset overturned the form book — Thomas Blake came in leading the head-to-head 1–0. Johan Kareld claimed a first win over Thomas Blake in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-20 | Sweden F1 | R16 | hard | Thomas Blake | 6-4 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.