The Primeira Liga champions were stunned at Boavista last weekend, while Estrela suffered defeat in their first game at this level.
Match preview
After a win in the Portuguese Super Cup against Porto, Benfica entered the season as favourites for the title once again.
However, Roger Schmidt's side made a mess of their season opener, losing 3-2 at Boavista despite taking the lead twice.
Petar Musa's red card ultimately proved fatal to Benfica's chances, and a shock defeat was confirmed in the 13th minute of injury time when Robert Bozenik took advantage of a non-existent Benfica defence to score the winner.
It was a first competitive defeat since Benfica's four-game winless run at the start of April.
Some alarming results in pre-season hinted towards a potential blip at the start of the season though, as the Eagles were beaten by both Feyenoord and Burnley.
The opening day defeat means that Boavista's city rivals Porto are now the favourites ahead of Benfica for the title.
Benfica now have five winnable games before they face Porto in one of the standout fixtures of the season, and they must realistically win all five.
This fixture will be a special occasion for Estrela as the phoenix side of the former club which went bust over a decade ago are now back at the top level.
They slumped to a 1-0 defeat against Vitoria Guimaraes on the opening day in an underwhelming performance though, and this matchup is set to be even tougher.
Recording zero shots on target after an early Miguel Lopes red card contributed heavily to their defeat, and a similar story could be written at the Estadio da Luz this weekend.
Estrela faltered late last season to concede an automatic promotion spot, but they sent Maritimo down in the relegation/promotion playoffs.
Despite the highs of that success, Estrela have won just two of their last eight competitive games - including a League Cup defeat to Portimonense before the league opener.
Sergio Vieira's side were also thrashed in all three pre-season friendlies, conceding 12 goals in games against Sporting Lisbon, Roma and Belenenses.
Benfica Primeira Liga form:
Benfica form (all competitions):
Estrela Amadora Primeira Liga form:
Estrela Amadora form (all competitions):
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Team News
Another summer of upheaval at Benfica has seen many more players come and go, with Alejandro Grimaldo and Goncalo Ramos among the big-name departures.
The club have made some very notable additions though, with Orkun Kokcu and Angel Di Maria both arriving.
Arthur Cabral has also been signed as Ramos's replacement following a stellar campaign with Fiorentina in Europe, and he could start given Musa's suspension.
David Jurasek made his league debut for the club last week after being signed from Slavia Prague to be Bayer Leverkusen-bound Grimaldo's replacement.
After his red card against Guimaraes, defender Lopes will miss out here for Estrela.
None of their new signings started in that defeat that last weekend, but two - Leo Cordeiro and Alioune Ndour - came on as substitutes.
Goals could be a worry as no player hit double figures for them last season and top scorer Paulinho has left for Portimonense.
Benfica possible starting lineup:
Vlachodimos; Bah, Antonio Silva, Otamendi, Jurasek; Joao Neves, Kokcu, Aursnes; Di Maria, Arthur Cabral, Rafa Silva
Estrela Amadora possible starting lineup:
Bruno Brigido; Mansur, Otieno, Gaspar; Jean Felipe, Vito Emanuel, Aloisio de Souza, Joao Reis; N'Do, Tavares, Ronald
We say: Benfica 6-0 Estrela Amadora
Motivated by an opening day defeat, Benfica may show no mercy on their newly-promoted visitors here.