The winner of this match will move on to the final four, where they will face either Santa Clara or Porto, who face off on Wednesday.
Match preview
Vitoria de Guimaraes are in search of what would be only their second-ever Taca de Portugal title and are featuring in the last eight of the competition for the first time since the 2018-19 season when they were beaten 1-0 by Benfica.
Os Vimaranense kicked off this season's competition with a 3-1 win over Moncarapachense, followed by a 4-1 victory against Vilaverdense and, most recently, a 1-0 win over Penafiel at the start of last month.
In league terms, Alvaro Pacheco's side have managed an impressive 39 points in 20 matches and are just one point behind Braga, who hold the fourth and final European qualification spot.
The hosts claimed their 12th league win of the season last weekend, beating Vizela 1-0 on the road and have lost only one match since the November international break, although notably, that defeat came against their opponents in this match just a couple of weeks ago.
Still, Os Branquinhos will be confident heading into this match as they have a very good home record this term, which includes six consecutive wins in all competitions ahead of this one, while they have only been defeated twice in 10 league games on home soil.
Meanwhile, Gil Vicente will be hoping that this will be the year that they can earn their first Taca de Portugal title, with their best-ever finish being a semi-final appearance, which they achieved in 2015-16 when they were beaten 5-0 on aggregate by Porto.
In the last three rounds, the visitors had to come from behind to beat Os Belenenses 2-1 before securing two more straightforward victories over FC Serpa (1-0) and Amarante (3-1) last month.
After bowing out of the competition in the fourth round in each of the last two editions, the Roosters will have genuine belief that they can reach the final four this term, especially after beating this opponent 1-0 last month.
Last weekend, Vitor Campelos's side suffered a 3-0 defeat at the hands of league leaders Benfica, which halted a run of four matches unbeaten in all competitions, including three wins and a draw.
However, Gil Vicente's away record this season has been very poor as they have only won one of their 10 league matches while suffering defeat in each of the other nine on the road.
Vitoria de Guimaraes Taca de Portugal form:
W
W
W
Vitoria de Guimaraes form (all competitions):
D
W
W
W
L
W
Gil Vicente Taca de Portugal form:
W
W
W
Gil Vicente form (all competitions):
L
W
D
W
W
L
Team News
Vitoria de Guimaraes will be without the services of Cape Verde midfielder Telmo Arcanjo, who remains sidelined due to a cruciate ligament tear he sustained last May.
Joao Silva came off the bench to score the winner against Penafiel in the last round and will be hoping to make the starting 11 in this match, possibly at the expense of Nuno Santos.
Gil Vicente will be able to welcome back Depu and Jonathan Buatu, who are returning from the Africa Cup of Nations with Angola, where they were knocked out of the competition by Nigeria in the quarter-final.
Stanislav Kritsyuk remains sidelined with a long-term injury and is likely to miss the remainder of the season, while Kiko is ruled out of action until March due to a knee injury.
Vitoria de Guimaraes possible starting lineup:
Varela; Fernandes, Borevkovic, Ribeiro; Gaspar, Handel, T. Silva, Mangas; J. Silva, A. Silva, Jardel
Gil Vicente possible starting lineup:
Andrew; Carlos, Pereira, Fernandes, Buta; Dominguez, Castillo, Neto, Costa; Fujimoto, Correia
We say: Vitoria de Guimaraes 2-1 Gil Vicente
While Gil Vicente did manage a hard-fought victory over this opponent just a couple of weeks ago, that victory came on their home patch, and they now have to head to Guimaraes, where Vitoria has been very good, currently holding the league's third-best record behind Sporting and Benfica.