Both sides head into the game fresh off the back of crashing out of the Taca de Portugal and will be looking to quickly bounce back to winning ways.
Match preview
Rio Ave's Taca de Portugal campaign came to an end last Sunday when they suffered a disappointing 3-2 loss at the hands of lower-tier Oliveira Hospital in extra-time.
After Rui Batalha scored a four-minute brace to cancel out Leonardo Ruiz's first-half opener and put the hosts ahead, Vitor Gomez netted his first goal of the season to force extra time, where Patrick grabbed a 116th-minute winner.
This was a second consecutive defeat for Luis Freire's men, who were beaten 4-2 by high-flying Benfica in their most recent Primeira Liga outing on October 8.
Rio Ave, who secured their return to the top flight last season courtesy of a first-placed finish in the Segunda Liga last term, have endured a slow start to the league campaign, managing just two wins from their opening nine matches.
With nine points from a possible 27, the Vilacondenses are currently 14th in the Primeira Liga standings, but could potentially move level on points with 10th-placed Chaves with all three points on Monday.
Like the hosts, Portimonense were dumped out of the Taca de Portugal last weekend when they suffered a shock 2-0 defeat against third-tier outfit Vilaverdense.
Former Benfica man Andre Soares opened the scoring at the Estadio Cruz do Reguengo to hand the hosts a first-half lead before Brazilian international Edmilson put the result beyond reach with a 92nd-minute effort.
Portimonense's cup defeat was in keeping with their struggles in the Primeira Liga, where they are currently on a two-game losing streak, suffering defeats against Vizela and Porto respectively.
Paulo Sergio's men have picked up five wins and lost four of their opening nine league matches to collect 15 points and sit in eighth place, level on points with seventh-placed Estoril Praia.
While the Portimao-based club will be looking to avoid a fourth consecutive loss for the first time since April, Monday's game pits them against an opposing side who they have failed to defeat in their last eight attempts, losing five and claiming three draws since a 4-1 victory in January 2018.
Rio Ave Primeira Liga form:
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Portimonense Primeira Liga form:
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Team News
Barring any late fitness issues, Rio Ave head into Monday's contest with a clean bill of health and no suspension concerns, giving Freire the luxury of a full strength squad at his disposal.
Aziz has been a standout performer for the home side this season, and the Ghanian striker, who has eight goal involvements in nine league games, will certainly be one to keep an eye out for.
Portimonense will have to make do with the absence of Portuguese midfielder Pedro Sa, who is set to sit out his fifth consecutive game after coming off injured in September's game versus Famalicao.
He is joined on the club's injury table by Brazilian international Anderson, who is yet to feature this season after sustaining a muscle injury back in May.
Twenty-eight-year-old Carlinhos adds to the visitor's midfield crisis as the former Vitoria de Setubal man picked up a severe injury against Sporting Lisbon back in May.
Rio Ave possible starting lineup:
Jhonatan; Sa, Santos, Nobrega; Costinha, Guga, Samaris, Gomes, Amaral; Aziz, Boateng
Portimonense possible starting lineup:
Nakamura; Moufi, Relvas, Guarapuava, Seck; Moreira, Luquinha, Jocu; Gomes. Cariello, Ewerton
We say: Rio Ave 1-1 Portimonense
Rio Ave and Portimonense will both be looking to restore some pride following their disappointing cup exit. Looking at past results between the sides, Rio Ave are slight favourites to come away with the desired results, but we predict the visitors will do just enough to force a share of the spoils.