Israel Monteiro advanced when Tiago Sousa retired 6-7 7-6 4-4 in the Portugal 5 Masters 3 round of 32. Israel Monteiro claimed a first win over Tiago Sousa in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-09-27 | Portugal 3 Masters 3 | R32 | hard | Tiago Sousa | 6-3 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.