Having lost each of their previous five matches, the Canarinhos are under pressure to turn things around against an opposing side whom they have failed to get the better of in their last 20 attempts since January 2013.
Match preview
Benfica ensured they remain within touching distance with Sporting Lisbon at the top of the Primeira Liga table as they picked up a 2-0 victory over Boavista at the Estadio da Luz on Friday.
Having failed to make their chances count in the first half, the breakthrough strike came thanks to Angel Di Maria shortly after the hour before substitute Marcos Leonardo put the result beyond reach in the 94th minute.
With that result, Roger Schmidt's side have now won eight games on the bounce across all competitions, including a 3-1 victory over Salzburg in the Champions League, where they finished third in Group D with four points from six matches.
Having won the Primeira Liga last season, Benfica's dreams of securing back-to-back league titles remain well on track as they sit second in the league table, just one point behind first-placed Sporting Lisbon.
As Aguias now turn their attention to the Taca da Liga, where they kicked off their quest for a record-extending eighth title with a 2-0 victory over Arouca at the Estadio Municipal de Arouca on October 31.
Benfica made light work of AVS in their second and final group-stage outing as they hammered the second-tier outfit 4-1 on December 21 to finish top of Group B with maximum points.
Having stormed through the qualifying phase, where they brushed aside Pacos de Ferreira and Belenenses, Estoril had to show their mettle in the group opener as they picked up a 2-1 win over Leixoes on September 27.
This was followed by a stunning 3-1 victory over defending champions Porto on December 6, when Cassiano, Rafik Guitane and Joao Carlos all found the back of the net to help the Canarinhos clinch top spot in Group D.
While Estoril will look to pick up right where they left off against Porto and reach a first-ever Taca de Liga final, their form heading into Wednesday has been nothing to write home about.
Vasco Seabra's men were on the receiving end of a 2-1 loss against Arouca at the Estadio Antonio Coimbra da Mota on Saturday, their fourth defeat in four matches across all competitions since the turn of the year.
This poor start to the year has been owing to their recent defensive vulnerability as they have shipped 14 goals in their last four matches, having conceded seven in the previous 10 matches preceding that run.
Standing between Estoril and a place in the cup final is a Benfica side who have won each of their most recent five meetings and are unbeaten in their last 20, claiming 18 wins and two draws since January 2013.
Benfica Taca da Liga form:
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Benfica form (all competitions):
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Estoril Praia Taca da Liga form:
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Estoril Praia form (all competitions):
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Team News
Benfica will take to the pitch without Danish striker Casper Tengstedt, who has been sidelined since sustaining a thigh injury in the cup victory against AVS back in December.
He is joined on As Aguias' injury table by fellow countryman Alexander Bah, who has been sidelined through a foot problem, while former Paris Saint-Germain man Juan Bernat is currently recuperating from a muscle injury.
Brazilian striker David Neres made his return from a two-month spell on the sidelines against Boavista last weekend and the 26-year-old should be named in the squad on Wednesday.
Scottish midfielder Jordan Holsgrove missed Estoril's game against Arouca after coming off injured versus Moreirense on January 13 and will play no part in Wednesday's game.
Alex Soares has also missed each of the Canarinhos' last seven matches since through injury, while Erick Cabaco continues his lengthy spell on the sidelines after suffering a severe muscle problem back in September.
Benfica possible starting lineup:
Trubin; Aursnes, Silva, Otamendi, Morato; Luis, Kokcu; Di Maria, Silva, Mario; Cabral
Estoril Praia possible starting lineup:
Carne; Parra, Volnei, Vital; Gomes, Fernandes, Koindredi, Araujo; Guitane, A Marques, J Marques
We say: Benfica 2-0 Estoril Praia
Estoril Praia are in for a tough 90 minutes against a high-flying Benfica side who have been near-perfect in recent weeks. Schmidt's men have been imperious in the history of this fixture and we fancy them claiming a comfortable victory once again.