The teams convene at Estadio Municipal after the hosts edged through the promotion/relegation playoffs in May; their opening day visitors managed to secure European football.
Match preview
Having consistently finished in Portugal's top 10 for over a decade, Vitoria de Guimaraes have established themselves as regular challengers for the 'best of the rest' tag, behind the Primeira Liga's established top four.
Last season, Os Conquistadores were able to claim sixth spot in the top flight: ending their campaign with a 5-0 thumping of fellow European challengers Gil Vicente.
Vitoria have grown accustomed to competing in continental competition, having reached the group stage of the Europa League three times in the past nine seasons, and are now taking part in Europa Conference League qualifying.
Despite losing both their top goalscorer - Colombian striker Oscar Estupinan, who departed for Championship side Hull City - and Saudi Arabia-bound coach Pepa, they made a positive start to the process.
Having dispatched Hungarian club Puskas Academy 3-0 over two legs, Vitoria took on Hajduk Split in the third round on Thursday, but a 3-1 defeat in Croatia leaves them with an uphill battle to progress. Nonetheless, they now kick off their domestic campaign as favourites for three points against relatively modest opposition.
New coach Moreno Teixeira leads his side to Chaves, near the Spanish border, following their hosts' elevation to the top flight via a third-place finish in Liga 2 and subsequent playoff win over Moreirense.
Chaves boss Vitor Campelos has since reshaped his squad, with 13 reinforcements already secured, including two Spanish forwards: Hector Hernandez (signed from Rayo Majadahonda) and Jonny Arriba (Villarreal B). However, star striker Wellington, the Flavienses' top scorer last season with 13 goals, has departed for Al-Arabi.
Now back in the big time, the Transmontans finished 11th in 2016-17 before coming sixth the following season, but then descended to the second tier in 2019.
While fifth place in 1987 represents the club's best-ever ranking in the top flight, the current squad would surely settle for any placing above the drop zone in their comeback campaign, and even a point on the opening day would be warmly welcomed.
Chaves form (all competitions):
Vitoria de Guimaraes form (all competitions):
Team News
In addition to their arrivals from Spain, Chaves have also secured experienced defender Steven Vitoria from Moreirense this summer, and the Canada international will be joined by fellow new boys Nelson Monte (ex-Almeria) and Sandro Cruz (on loan from Benfica) in the hosts' squad on Monday.
Last year's mainstays, such as goalkeeper Paulo Vitor, midfield pair Joao Teixeira and Nwankwo Obiora, and defender Joao Correia have all been retained, too.
All four could start in the season opener, while - with a record of 16 goals and seven assists for Villarreal B last season - Jonny Arriba is pushing to start alongside his compatriot Hector Hernandez up front.
Vitoria, meanwhile, have made seven reinforcements so far, with left-back Ryoya Ogawa and forwards Jota Silva and Andre Silva having already featured in the Conference League qualifiers.
However, winger Rochinha has moved to Sporting, after scoring 19 times in 122 appearances over the past four seasons, and Oscar Estupinan is settling into life in England.
Midfielder Andre Almeida recently returned from a muscular injury and is expected to feature on Monday, while both Jorge Fernandes and Tomas Handel should overcome knocks to make the trip north.
Like Almeida, young right-back Miguel Maga also played against Hajduk Split, scoring a superb goal in the 3-1 defeat, and is set to start in the visitors' back four.
Chaves possible starting lineup:
Vitor; Correia, Monte, Vitoria, Langa; Pina, Obiora, Teixeira, Juninho; Patrick, Hernandez
Vitoria de Guimaraes possible starting lineup:
Varela; Maga, Mumin, Villanueva, Ogawa; Almeida, Handel, Semedo; Lameiras, Anderson, Jota
We say: Chaves 1-2 Vitoria de Guimaraes
Having the benefit of three competitive games already under their belts, Vitoria can overcome the loss of some important figures to start with a win against promoted opponents.