Tiago Cacao defeated Pablo Vivero Gonzalez 1-6 7-6 6-3 in the M25+H Oliveira De Azemeis 1 round of 16 on hard. The upset overturned the form book — Pablo Vivero Gonzalez came in leading the head-to-head 4–1, but Tiago Cacao had been the form player, winning 4 of their last 4 on hard. Tiago Cacao narrowed the head-to-head to 4–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-10-03 | M25 Tavira 1 | R16 | hard | Tiago Cacao | 6-4 7-6(4) |
| 2018-03-26 | Portugal F6 | R32 | hard | Pablo Vivero Gonzalez | 6-1 6-4 |
| 2018-02-26 | Portugal F2 | R32 | hard | Pablo Vivero Gonzalez | 6-3 6-0 |
| 2016-11-21 | Spain F38 | R16 | hard | Pablo Vivero Gonzalez | 6-1 6-4 |
| 2015-07-27 | Portugal F11 | QF | hard | Pablo Vivero Gonzalez | 4-6 7-5 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.