Sergio Vieira's men are currently just 90 minutes away from a first-ever Portuguese top-flight appearance after picking up a 2-1 victory in the first leg last Saturday.
Following a truly forgettable Primeira Liga campaign, Maritimo finished just above the automatic drop zone to battle it out over two legs in the relegation playoffs.
Jose Manuel Gomes's men went into the first leg knowing history was not on their side, with the top-tier side failing to retain their status since the introduction of the relegation playoffs three seasons ago.
However, former Internacional man Claudio Winck grabbed a huge goal for O Maior das Ilhas when he pulled one back in the 87th minute to hand them a fighting chance at the Estadio do Maritimo.
While Maritimo will be looking to turn their fortunes around, they have picked up just one win from a losing position all season, which came back in February, when they came from behind to secure a 3-1 victory over relegated Santa Clara.
After a sour end to their Segunda Liga campaign, Estrela Amadora will be delighted with the position they have put themselves in ahead of this weekend's second leg.
The Tricolores looked set to be amongst the two sides gaining automatic promotion from the second tier when they went unbeaten in their first 16 league games in 2023, claiming 10 wins and six draws in that time.
Disappointingly, a run of four points from their final four games of the season saw Vieira's men drop to third, with Farense jumping into second place with wins in each of their final eight matches.
Last Saturday's victory rekindled hopes of a first-ever Primeira Liga appearance, just three years after Clube Desportivo Estrela and Club Sintra Football merged to form the Lisbon outfit.
While Estrela have placed one foot in the top flight, the job is not done yet, as they visit the Estadio do Maritimo, where the hosts are unbeaten in four of their last five matches, claiming three wins and one draw since the start of April.
Maritimo will still have to cope without the services of Italian forward Stefano Beltrame, who has been sidelined since March through a muscle problem.
He is joined on O Maior das Ilhas' injury table by Czech Republic goalkeeper Matous Trmal, who is yet to make an appearance this year after sustaining an injury back in December.
Off the back of an inspiring cameo, Winck could be rewarded with a starting role on Sunday as we expect Gomes to name his strongest possible XI for this weekend's must-win tie.
Maritimo possible starting lineup:
Carne; Mota, Zainadine, Mosquera, Costa; Winck, Xadas, Vidigal; Catamo, Riascos, Correia
Estrela Amadora possible starting lineup:
Brigido; Gaspar, Lopes, Mansur; Reis, Guzman, Vito, Felipe; Ndo, Tavares, Ronald
We say: Maritimo 1-1 Estrela Amadora
With just 90 minutes separating Estrela and Primeira Liga football, we expect the Lisbon outfit to leave everything on the pitch this weekend. Last week's result has put Vieira's side in pole position and we predict they will hold out for a draw to win on aggregate.
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