Diogo António Cupido Gonçalves was born in Almodôvar, in the Alentejo, and joined Benfica's academy in 2008. He progressed to the B team in 2015 and made his first-team debut in August 2017 in a Primeira Liga win over Braga, having already featured in the Supertaça.

A winger comfortable on either flank, he was loaned to Nottingham Forest in 2018/19 and to Famalicão in 2019/20, the latter spell earning him a recall to the Benfica squad. He was a rotation option over the following seasons and produced his most productive spell in 2021/22, when he scored six league goals.

Under Roger Schmidt in 2022/23 his minutes were limited by the form of the wide players ahead of him, and he made only a handful of appearances before the winter break. On 5 January 2023 he joined FC Copenhagen on a four-year contract, leaving Benfica after roughly 90 competitive appearances and two Primeira Liga titles.