Juan Pino defeated Bertrand Madsen 6-4 6-4 in the Caribbean 1 Masters 2 qualifying round on clay. The upset overturned the form book — Bertrand Madsen came in leading the head-to-head 1–0. Juan Pino claimed a first win over Bertrand Madsen in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1993-04-24 | Caribbean 1 Masters 1 | R16 | clay | Bertrand Madsen | 7-6 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.