While the hosts are seeking to secure a first-ever top-flight appearance, O Maior das Ilhas look to end their horror campaign on a high by retaining their Primeira Liga status for another season.
Match preview
Just three years after Clube Desportivo Estrela and Club Sintra Football merged to form Estrela Amadora, the club are now on the cusp of a first-ever appearance in the top flight.
The Lisbon outfit finished third in the Segunda Liga, picking up 16 wins and 15 draws in their 34 matches to collect 63 points, six points off second-placed Farense in the automatic promotion spot.
Sergio Vieira's men looked set to seal automatic promotion, when they went undefeated in each of their first 16 league matches in 2023, claiming 10 wins and two draws in that time.
However, a run of just one point from their three matches leading up to the season finale saw Farense, who racked up eight straight wins in their final eight outings, snatch second position.
Estrela wrapped up the Segunda Liga campaign in style, thrashing Penafiel 4-2 on May 27 courtesy of goals from Jean Felipe, Joao Reis, Joao Silva and Angolan forward Capita.
On the other hand, Maritimo's 14-year spell in the Portuguese Primeira Liga has come under threat following what has been nothing short of a truly forgettable campaign.
The O Maior das Ilhas picked up just 26 points from their 34 matches to finish eight points adrift of 15th-placed Portimonense in safety and just three points above the automatic drop zone.
Jose Manuel Gomes's men lost 22 league matches — with only relegated Pacos de Ferreira suffering more defeats — while conceding the highest number of goals last season (63).
Maritimo managed just one win in their final six games of the Primeira Liga campaign, which came on May 19 when they edged out Vizela 1-0 at the Estadio do Maritimo thanks to a 95th-minute effort from Claudio Winck.
Since the introduction of the relegation playoffs three seasons ago, the top-tier club have failed to retain their status, a record Maritimo will be looking to break as they head into Saturday's first leg.
Estrela Amadora form (all competitions):
L
L
D
Maritimo Primeira Liga form:
L
L
D
L
W
L
Team News
Estrela will have to cope without centre-back Johnstone Omurwa, who will miss the first leg through suspension after picking up a red card in the season finale against Penafiel on May 27.
In his absence, Angolan international Kialonda Gaspar should come into the fold, forming the back three with Rui Correia and former Chaves full-back Joao Reis.
Former Real Betis forward Regis Ndo has played a huge role in attack for Estela this season and should retain his role in the XI, alongside Belenenses loanee Kikas, who has 10 league goals to his name.
Maritimo will be without the services of Rene Santos and Fabio China, who are both suspended after picking up red cards in the Primeira Liga final-day showdown against Estoril Praia.
On the injury front, Gomes will be unable to call upon Czech Republic goalkeeper Matous Trmal, who has been sidelined since December through a severe injury.
He is joined on O Maior das Ilhas' injury table by Italian forward Stefano Beltrame, who has been out of action since March through a muscle problem.
Estrela Amadora possible starting lineup:
Filipe; Correia, Gaspar, Reis; Camargos, Guzman, Fall, Felipe; Ndo, Kikas, Silva
Maritimo possible starting lineup:
Carne; Paulinho, Zainadine, Mosquera, Costa; Afonso, Xadas, Vidigal; Catamo, Riascos, Correia
We say: Estrela Amadora 2-1 Maritimo
Estrela Anadora were left spitting feathers after a slight slump in form denied them an automatic spot in the Bundesliga. However, they take on a spineless Maritimo side who have struggled to win games and should take their first-leg win in front of their home supporters.