Second division side Estoril Praia host Benfica in the first leg of the Taca de Portugal semi-final on Thursday evening.
The Canarinhos have never lifted the trophy before in their history, while the visitors have claimed the cup on 26 occasions.
Match preview
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Bruno Pinheiro's men are enjoying a successful season so far. They are currently sitting in second place in the LigaPro standings, and also reached the quarter-finals of the Taca da Liga earlier in the campaign.
The Estadio Antonio Coimbra da Mota outfit have already defied the odds on several occasions to reach the last four of the competition.
Estoril have seen off three top-flight sides in the shape of Boavista, Rio Ave and Maritimo in previous rounds but will know Benfica pose their biggest challenge yet.
Pinheiro's side will have to try and cope without their main threat on Thursday, though. Twenty-one-year-old striker Abdul-Aziz Yakubu, who is on loan from Vitoria de Guimaraes, has bagged 10 goals in all competitions this season, including three in the Taca de Portugal, and his absence will be a huge blow for the second-tier team.
If Estoril do manage to pull off one of the biggest shocks in modern Portuguese footballing memory, then a positive result on home soil will surely be required. They will know the task they face is huge but will be able to play without any fear or pressure, and that could prove to be pivotal over the two legs.
Benfica defeated Belenenses 3-0 in the quarter-finals to reach this stage and will be hoping they can progress to the showpiece event for the second year in a row.
As Aguias were defeated in the 2019-20 final by fierce rivals Porto and will be desperate to avenge that crushing loss this time around.
Jorge Jesus's men picked up a valuable victory last time out when they took on Famalicao, ending a run of four league games without a win.
That performance on Monday will have restored the confidence and belief within the Estadio da Luz outfit ahead of this midweek encounter.
It is a fixture that could have serious consequences for Jesus if his side fails to put in a strong showing and secure an advantage heading into the second leg given the strain that the 66-year old's position is already under.
Estoril Praia Taca de Portugal form: WWWWW
Estoril Praia form (all competitions): WDDWLL
Benfica Taca de Portugal form: WWWW
Benfica form (all competitions): LDWLDW
Team News
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As previously mentioned, Estoril will be without their main goal threat Abdul-Aziz Yakubu, who is suffering from an injury and has not recovered in time to play any part in this one.
Winger Harramiz was sent off last time out after picking up two yellow cards against Academia and will be suspended for this cup tie.
Long-term absentee Andre Almeida is once again unavailable for Jesus as the experienced full-back continues to recover from a ruptured cruciate ligament.
He is joined on the sidelines by striker Luca Waldschmidt, winger Rafa Silva and 34-year-old central-defender Jardel.
Estoril Praia possible starting lineup:
Thiago; Basto, Soria, Gomes, Joaozinho; Crespo, Gamboa; Valente, Lourenco, Vidigal; Franco
Benfica possible starting lineup:
Vlachodimos; Gilberto, Otamendi, Vertonghen, Grimaldo; Weigl, Taarabt; Everton, Cervi; Seferovic, Nunez
We say: Estoril Praia 0-2 Benfica
Estoril have done amazingly to get this far, and although another upset is potentially on the cards, we fancy Benfica to put in a strong showing and take control of the tie. The extra quality on offer within the capital club's ranks should see them take a healthy advantage back to the Estadio da Luz.
Top betting tip
George Cannon
