It was in the 1960s, that Angrense achieved its highest point, when it won the insular, Azorean and district championships during the 1959-60 seasons. A large crowd was present on 3 May 1960, in the Angra do Heroísmo Game Field, to watch the game between Angrense and Marítimo of Madeira, during the quarter finals of the Portuguese Cup. Angrense won this championship over Marítimo 2-1, while the secondary game was decided in a draw. For the first time in regional football history, an Azorean team participated in the Portuguese Cup, against the national champion and benefactor, Benfica. Benfica's first trip to the Azores for a championship, the team arrived on 4 June 1960, to the enthusiasm of local spectators and supporters, and members of the team travelled, not only to Terceira, but to the islands of Faial and São Miguel, where they were met was adulation. In the final, Benfica won 2-0 on 5 June 1960, and later soundly defeated Angrense 10-0 in the return engagement in the Estádio da Luz, Lisbon, on 12 June.