Juan Pablo Canas Garcia defeated Terence Das 6-3 6-4 in the M15 Vale Do Lobo 1 q16 on hard. The upset overturned the form book — Terence Das came in leading the head-to-head 2–1. Juan Pablo Canas Garcia narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2020-03-09 | M15 Loule 1 | Q32 | hard | Terence Das | 6-2 1-0 |
| 2019-07-09 | M15 Idanha-A-Nova 2 | Q16 | hard | Juan Pablo Canas Garcia | 6-4 6-4 |
| 2019-07-02 | M15 Idanha-A-Nova 1 | Q16 | hard | Terence Das | 6-3 5-7 10-3 |