He won the 2016 Rio Open by defeating Rafael Nadal in the semifinals and Argentine Guido Pella in the final. The next week, he won the Brasil Open in São Paulo by defeating Spaniard Pablo Carreño Busta in the final. He was the runner up at the 2016 Nottingham Open to Steve Johnson. He was runner up at the 2016 German Open to Martin Klizan. Cuevas struggled to put together wins over the rest of the year, falling in the second round at the 2016 Rio Olympics and the 2016 US Open.