The day Estrela da Amadora knocked out Vitória SC on their way to Portuguese Cup glory | OneFootball

It is hard to imagine now how the Portuguese Cup was once a paradise for minnows. Come the late 1980s and across the following decade the competition hosted some of the most remarkable and incredible fairytales in the whole history of the Portuguese game.

Few were so dramatic and unexpected as the rise of Estrela da Amadora from unknown neighbourhood club into national royalty. Something that, in Guimarães, home of one of Portugal’s greatest, albeit perennially underperforming sides, is still a hard pill to swallow, thirty-four years on.

On the weekend Estrela welcome Vitória to the Estádio José Gomes in the Liga Portugal, football historian Miguel Lourenço Pereira looks back at Estrela’s finest hour.

Big Three fall by the wayside early

Nobody expected it. When news came of Tirsense’s surprising win at the Antas stadium on February 27th against favourites FC Porto, nationwide supporters realised something out of the ordinary had just happened. For the first time in many years there was no representation of the so-called Big Three in the Taça de Portugal last eight. Not in the final nor the semis. The last eight. It meant eight football clubs unaccustomed to lifting a trophy would find the chance of their lives right at their doorstep.

Benfica and Sporting were already out, beaten by Vitória FC and Marítimo in the previous rounds. The Dragões defeat made things even more interesting. There was still a third division side in the final run – UD Valonguense – and two from the second division, Farense and Maia, who were all seen as appetising opponents for the now favourites Vitória FC, Vitória SC and holders Belenenses.

Setúbal and Belenenses were pitted against each other and the Belém side came out victors only after a floodlight failure at Bonfim granted them a 0-3 win, after a controversial decision by the Portuguese Federation. Meanwhile the other Vitória, suffered more than initially expected to beat Maia, and became front-runners to beat Estrela da Amadora in the semifinals, after Estrela had edged out Porto’s nemesis Tirsense.

Portuguese Cup 1989/90 semi-final lineup

Estrela da Amadora v Vitória SC

Belenenses v Farense

The Guimarães side had already dispatched Vila Real, Freamunde and Macedo de Cavaleiros and where yet to play a first-division side. In town many dreamed already with a chance of finally clinching a trophy after winning the Supertaça two years previously. It was a side full of well-respected players, from goalkeeper Neno up to the likes of Soeiro, N’Dinga, Basílio and Chiquinho Carlos, well coached by Brazilian manager Paulo Autuori, who would in the following years become a household name thanks to the exploits of his Marítimo side that eventually led Benfica to hire his services. Pitted against the Minho side was Estrela da Amadora, still living its first years of professional football.

Estrela was an odd football club in Portuguese football of the late 1980s. At a time when the shift of power was moving north, with more and more teams from north of Porto, in the areas between the Ave and Cávado Rivers, getting promoted to the first division, Estrela rose to the elite for the first time in their history in 1988. Amadora was thought to be a troubled suburban town right outside Lisbon, known especially for its African community, mixed with many forced to return from the former imperial colonies fifteen years before. (As an aside, just this week, 34 years later, the zone of Amadora is in the headlines in Portugal after disturbances in its own and nearby neighbourhoods).

Unfashionable but on the up

It was a world that was very distant to the capital’s glamour lifestyle just a few miles south. Yet, while a lot was happening in the streets surrounding Amadora – with the seeds of the hip-hop movement crossing paths with some hard-rock sounds brewing in the Brandoa neighbourhood from where the Moonspell group came from – the football club had managed to transform the Reboleira stadium into a living hell for any visiting side. In their first season at the top, Estrela ended in a brilliant eight place. The following season was less successful – 13th in the final league table – but paved way for a brilliant cup run.

The team coached by Boavista and Benfica former international glory João Alves, saw out nearby Estoril, and forced a play-off only decided on penalties against Sporting Braga. They then beat out Tirsense to claim a place in the semis. For many observers that was as good as it would get. Only things didn’t work out that way. There were plenty of talented names at Alves’ disposal although many were still unknown at the time. Paulo Bento was far from becoming the international footballer of later years but was already bossing around the midfield surrounded by the likes of Basaúla, Caetano and Bobó. Ricky, later the league’s top scorer with Boavista, was scoring freely while Duilio, Rebelo and Barny patrolled the defence.

All square and a replay up north

In front of packed stadium, things started sourly with João Gabriel netting the first after a dubious penalty awarded by Bento Marques. Estrela keep pressing forward and finally got their reward on the brink of half-time with Nigerian forward Ricky scoring the well-deserved equaliser. The match was a tense affair from then onwards, moving to extra time to no avail. No further goals were scored and a replay at the Dom Afonso Henriques stadium would decide who would accompany surprise-package Farense in the Cup Final.

Guimarães woke up a week later in celebratory mood. Many already saw Vitória on their way to Jamor and having to beat second-division Farense seemed a task even easier than to get rid of the recent first-division newcomers from Amadora. The area around the D. Afonso Henriques stadium was full from the earliest hour as many hard-core supporters decided to press the home advantage to the fullest. An early goal by Chiquinho Carlos seemed to be the goal everyone was expecting, coming at the 30th minute pretty much in the run of play. Vitória were flying and perhaps the ectasis of the celebration ended up playing against them.

On the brink of half-time, once again showing a never-say-die character, Estrela equalised from a set-piece. Nerves started to set in around the stands and as the ninety minutes ticked down, and Estrela started to believe that, like they had done with Sporting Braga, a miracle was on the horizon. They just needed to believe. And they did.

Basaúla kills his parent club

It fell to a loanee Guimarães player, Basaúla, the honour of scoring the most important goal in the history of Estrela up to that point. The Congolese midfielder – who alongside N’Dinga was destined for Belgium when Pimenta Machado managed to sign him for his Vitória side, unaware of what fate would bring – would eventually return to Guimarães the following season for a successful five-year spell but many never forgave him having netted the goal that prevented Vitória SC from reaching the final.

Only a club like Vitória could lose such an important match at the hands of a player from their own ranks. It would take almost twenty-five years before the Conquistadores finally clinched their sole Taça de Portugal trophy in a final against Benfica in 2013.

Estrela da Amadora win the Portuguese Cup and qualify for Europe after beating Farense in the 1990 final

In Amadora nobody expected the side to progress that far and celebrations went on all night long. Estrela eventually came out winners but only after playing a replay in the final, after drawing against Farense in the first game played at Jamor. They would take part in the following season’s Cup Winner’s Cup, winning the first round against Neuxatel Xamax from Switzerland only to be beaten by RFC Liége in the last sixteen round.

They were relegated at the end of that season but were back in 1993 staying among the elite for the remaining of the decade, especially thanks to the work developed by Fernando Santos, who had the side reaching seventh in 1998, their highest position ever, an achievement that paved the way for his move north to Porto. Estrela briefly returned to the first division in the mid-2000s but financial issues, like with so many clubs that peaked in the late 1980s and early 1990s, almost took them to the brink of disappearing.

The renewed club, a fusion between CD Estrela and Sintrense, opened the doors for first division football once again in the last couple of seasons, although many claim the club that now plays as Estrela cannot be mistaken with the old Estrela da Amadora side. The one that once silenced Guimarães before touching the Jamor sky with arms wide open.