Massimo Calvelli defeated Jiri Pelikan 6-4 4-6 6-4 in the Portugal 3 Masters 1 qualifying round on hard. The upset overturned the form book — Jiri Pelikan came in leading the head-to-head 2–0. Massimo Calvelli claimed a first win over Jiri Pelikan in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1993-08-21 | Slovak Republic Masters 1 | R16 | clay | Jiri Pelikan | 6-2 6-3 |
| 1992-09-28 | Portugal 3 Masters 3 | R16 | hard | Jiri Pelikan | 4-6 6-3 6-0 |