Sitting just a point above their hosts, Belenenses must avoid defeat at Estadio Municipal de Portimao to remain out of immediate trouble at the bottom end of the table.
Portimonense currently sit in 10th position in the form table, claiming seven points from their last six games in Portugal's top flight.
However, the home side are still playing catch-up after their slow start to the campaign, leaving them to sit alongside Famalicao in the bottom two.
Despite their comprehensive 3-0 reverse at Rio Ave last time out, Paulo Sergio will be optimistic about his team's chances of eventually moving away from trouble.
Portimonense have now suffered five successive setbacks on the road, but losing just twice from six fixtures on home territory is the major positive of the season so far.
Opponents Belenenses have endured a difficult time on the league front, collecting just one point from their four most recent matches.
Nevertheless, their 2-0 defeat at home to Pacos de Ferreira on Sunday equalled their heaviest loss for the season, highlighting that they have done an effective job in keeping themselves in matches.
Belenenses head into this game on the back of a thrilling 3-2 victory over Fafe in the Taca de Portugal, earning the club a quarter-final tie at Benfica later this month.
Trailing in the 88th minute, Nuno Oliveira's side netted two late penalties before a 119th-minute goal in extra time completed the most dramatic of turnarounds.
Even if the physical and emotional demand of that fixture has taken something out of Belenenses, they will still be on a high when they take to the pitch on Monday night.
Portimonense Primeira Liga form: WLDLWL
Belenenses Primeira Liga form: DWLLDL
Belenenses form (all competitions): LWLDLW
Sergio is expected to hand a start to Bruno Moreira, who has left Rio Ave to link up with Portimonense.
The home side are also boosted by the return of Dener after the midfielder served his suspension.
Miguel Cardoso will lead the line for the visitors after playing a key role in Belenenses's fightback in the cup on Thursday.
Portimonense possible starting lineup:
Samuel; Moufi, Antonio, Possignolo, Anzai; Luquinhas, Willyan, Dener; Morte, Moreira, Oliveira
Belenenses possible starting lineup:
Kritsyuk; Esgaio, Cafu, Silva, Henrique, Lima; Teixeira, Ramires, Caue, Sousa; Cardoso
We say: Portimonense 1-1 Belenenses
Even at this stage of the season, every point is vital in the bottom half of the Primeira Liga standings, and that could lead to a tense affair playing out on Monday evening. Neither side will want to lose, which could result in a largely uneventful draw occurring at Estadio Municipal de Portimao.