Still licking their wounds from their recent Taca de Portugal exit, the visitors will head into this one looking to snap their six-game losing streak and get their season back on track.
Match preview
Gil Vicente were sent home empty handed once again as they suffered a 1-0 defeat against 10-man Boavista when the sides met at the Estadio do Bessa last Sunday.
In a game where defender Reggie Cannon picked up his second red card of the season, 29-year-old Yusupha Njie came up clutch for the hosts as he netted the only goal of the game shortly after the half-hour mark.
Gil Vicente have now lost each of their last four away games in the Primeira Liga, conceding 10 goals and scoring just three since September's 2-1 victory over Maritimo at the Estadio do Maritimo.
Daniel Sousa's men head into Monday winless in all but one of their last nine league matches, picking up one draw and losing seven matches since September.
However, they return home, where they are on a run of two successive wins, beating Nacional 2-0 in the Taca da Liga on November 27 to end an eight-game winless home run before seeing off Santa Clara 1-0 in their final outing of 2022.
With 12 points from 16 matches, Gil Vicente are currently 16th in the Primeira Liga standings, two points adrift of 15th-placed Santa Clara just outside the relegation playoff spot.
Vitoria de Guimaraes, on the other hand, were dumped out of the Taca de Portugal as they suffered a 3-2 defeat at the hands of Braga after bottling a two-goal lead in the final 10 minutes.
In a nail-biting final 10 minutes at the Estadio Braga Municipal, a brace from Spanish forward Abel Ruiz and Vitinha's 82nd-minute strike saw Artur Jorge's side fight back from two goals down to book their place in the cup quarter-finals.
Os Vimaranenses have now failed to win any of their last six matches across all competitions, a run which also saw them crash out of the Taca da Liga after picking up three draws from three games and finishing second in Group F.
However, Joao Teixeira's men are on a decent run in the Primeira Liga, where they are unbeaten in eight of their last 10 matches, claiming five wins and three draws, including last Saturday's goalless draw against Rio Ave at the Dom Afonso Henriques.
Vitoria de Guimaraes have picked up seven wins, three draws and lost five of their 15 league matches this season to collect 24 points and sit sixth in the table, three points off fifth-placed Casa Pia in the final Conference League playoff spot.
Gil Vicente Primeira Liga form:
L
L
L
L
W
L
Gil Vicente form (all competitions):
D
W
W
L
W
L
Vitoria de Guimaraes Primeira Liga form:
W
W
L
W
L
D
Vitoria de Guimaraes form (all competitions):
D
D
D
L
D
L
Team News
Gil Vicente will be without the services of Brazilian forward Lucas Barros, who is yet to make his debut since joining last summer after picking up an injury in May.
He is joined on the club's injury table by Andrew Ventura, who has missed each of the last five matches since picking up an injury in November.
Meanwhile, Vitoria de Guimaraes remain without Portuguese midfielder Tomas Handel, who continues his long journey to full fitness after suffering a knee injury last February.
Fellow countryman Jose Carlos is also a major doubt for Monday's trip to the Estadio Cidade de Barcelos, having missed each of the last three matches through injury.
Strike partners Jota Silva and Anderson Siva were both on target in last week's cup defeat against Braga and we expect the duo to spearhead the visitors' attack for the second consecutive game.
Gil Vicente possible starting lineup:
Kritsyuk; Carraca, Lopes, Araujo; Marin, Carvalho, Aburjania, Souza; Fujimoto, Medina, Navarro
Vitoria de Guimaraes possible starting lineup:
Varela; Amaro, Bamba, Villanueva; Maga, Silva, Andre, Sa; Silva, Johnston, Silva
We say: Gil Vicente 1-1 Vitoria de Guimaraes
On a run of two successive home wins, Gli Vicente will fancy themselves to come away with the desired result in front of their home fans on Monday. However, we predict Vitoria de Guimaraes will do just enough to leave with a share of the spoils.