Sem Wensveen defeated Taylor Cataldi 6-4 4-6 6-3 in the W15 Monastir 19 round of 32 on hard. The upset overturned the form book — Taylor Cataldi came in leading the head-to-head 1–0. Sem Wensveen claimed a first win over Taylor Cataldi in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2021-05-18 | W15 Monastir 18 | Q16 | hard | Taylor Cataldi | 6-4 0-6 10-2 |