The 1990 Taça de Portugal final went down in history as the day of the underdogs. At the Jamor stadium Estrela da Amadora, recently promoted to the top flight, faced second-division Farense, and the first match, played on 3 June 1990, ended 1–1 after extra time. Only the replay, won 2–0 by Estrela, gave the club from the Lisbon suburbs the only major trophy in its history. Earlier, in the semi-final, the team had eliminated Vitória SC, and on the way to the final it also beat Tirsense. It is a triumph that remains Amadora's point of reference to this day.
The original club, Clube de Futebol Estrela da Amadora, was founded on 22 January 1932. It reached the top flight after a long journey, but once there it established itself in the 1980s and 1990s. In 1992–93 it won the second division. Estrela were never one of the big clubs of the Lisbon region, but they built an identity around working-class Amadora and their tricolour kit of red, white and green, which gave rise to the nickname 'Tricolores'. The home ground is the Estádio José Gomes in the Reboleira district, holding about 9,000 spectators, known for its closeness of the stands to the pitch and uncomfortable for many bigger opponents.
Winning the Taça de Portugal earned the club a place in the Cup Winners' Cup in 1990–91, the only European episode in its history. In the first round Estrela drew 1–1 twice with Switzerland's Neuchâtel Xamax and went through on penalties, 4–3. In the second round it lost to Belgium's RFC Liège 2–1 on aggregate, after a 2–0 defeat in the first leg and a 1–0 win in the return. In the same season the manager was Manuel Fernandes and his assistant was José Mourinho, for whom this was one of the first episodes of his coaching work in the top division. The season ended, however, with relegation: Estrela finished 18th.
The following decades brought a gradual weakening of the club, and in 2011 the original organisation collapsed because of financial problems and bankruptcy. An attempt was made to preserve the tradition by creating Clube Desportivo Estrela, which continued the youth teams and other sections. In July 2020 members voted 92 per cent in favour of merging CD Estrela with Club Sintra Football. A new public limited company was formed under the name Club Football Estrela da Amadora, which took Sintra's place in the third tier, the Campeonato de Portugal, and took over the historic colours and crest. Formally it is a new entity that did not take over its predecessor's honours, although it builds on its tradition and on the same ground.
The rebuilding was swift. The club was promoted after its first season, despite losing 1–0 to Trofense in the Campeonato de Portugal final, and in 2022–23 it won promotion to the Primeira Liga, settling the decisive tie against Marítimo on penalties. It made its top-flight debut in 2023–24, finishing 14th. André Geraldes has been president since the start of the new project.
Today Estrela da Amadora is a club that joins two eras. On the one hand it cherishes the memory of its cup triumph of years ago, and on the other it benefits from the opportunities that professional football has opened up. A smaller budget than the biggest rivals means that the team relies on a well-chosen, international squad and on the atmosphere of its own ground. In Portuguese football it remains an example of a club that was able to rebuild after collapse and preserve the heritage of the district it grew out of.