After a strong first half of last season, Sunday's hosts eventually dropped to seventh spot, while their visitors prevailed in the battle for survival, finishing in 14th place in the Portuguese top flight.
Vitoria de Guimaraes certainly had a season of two halves last year, with a strong start seeing them occupy fifth spot after the turn of the year.
Under the management of Joao Henriques, Os Vimaranenses dropped to sixth spot, and they would hold onto that position until the penultimate game of the campaign.
However, a poor run at the end of the season, collecting just 11 points from the final 16 games, saw the gap between the top six and the chasing pack slowly close, and they were finally overtaken on the last day of the campaign by Santa Clara, missing out on European football as a result.
However, they certainly have reason to be optimistic for the upcoming season following the appointment of Pepa, who guided Pacos de Ferreira to a fifth-placed finish last season.
In his first games in charge of the Guimaraes outfit, he took them through the first two rounds of the Taca da Liga, first defeating Leixoes as Diogo Rochinha, Bruno Duarte and Matheus Magalhaes got on the scoresheet alongside a Diogo Gomes own goal in a 4-1 win.
Duarte would again get on the scoresheet last time out, as they progressed to the third round with a 1-0 away win over Casa Pia, meaning Pepa will take his team into the season on the back of consecutive competitive victories.
They will face a different challenge on Sunday though, taking on Portimonense in a difficult clash to begin the league campaign.
After 13 games of last season, Paulo Sergio's side sat at the foot of the Primeira Liga table with just 11 points, but a crucial 1-0 win over Belenenses saw them quickly rise out of the drop zone.
The Algarve side would not fall into the bottom three for the remainder of the season, despite a mixed run of form, as they eventually finished in 14th spot, just one point above Rio Ave in the relegation playoff place and four points above the automatic drop zone.
While they did achieve the ultimate goal of avoiding relegation to the second tier, Sergio will hope for an improvement in the upcoming campaign, with his side looking to enter the battle for a top-half finish this time around.
Their Taca da Liga form has not provided much reason for positivity, though, as they scraped past second-tier Academica before being dumped out in the second round by Boavista last time out.
In that game, Tiago Morais netted a brace to fire Boavista to a fairly routine 2-0 victory, as Sergio's men looked uninspired heading into the new campaign.
They will have to put that result behind them and start afresh on Sunday if they are to build momentum with a strong start.
Vitoria de Guimaraes come into Sunday's game without first-choice goalkeeper Bruno Varela through injury, and Diogo Rochinha, who will serve a suspension.
Another change from the familiar starting XI is the absence of midfielder Pepelu, who returned to Levante after a loan spell last season.
Os Vimaranenses did address the gap in midfield with the capture of Alfa Semedo, who impressed in the Championship last season while on loan at Reading from Portuguese giants Benfica.
Toni Borevkovic also arrived from Rio Ave to add another option in defence, and the centre-back could come straight into the side on Sunday.
Portimonense have given their squad a major boost with the signings of Payam, Casagrande, Pedrao and Ivan Angulo, but they must quarantine before joining the squad and will not be available for selection on Sunday.
However, midfielder Giannelli Imbula is now free to play, having been ineligible after arriving as a free agent late last season.
The attacking line will be led by Beto, who netted 11 goals and registered three assists in 30 Primeira Liga appearances last season.
Vitoria de Guimaraes possible starting lineup:
Trmal; Sacko, Fernandes, Borevkovic, Soares; Andre, Semedo, Almeida; Quaresma, Estupinan, Edwards
Portimonense possible starting lineup:
Samuel; Moufi, Willyan, Possignolo, Cande; Fernandes, Imbula, Carlinhos; Salmani, Beto, Boa Morte
We say: Vitoria de Guimaraes 2-0 Portimonense
While Vitoria de Guimaraes did not always live up to expectations last season, they still boast a stronger squad than Sunday's opponents, and should get over the line to start the season with three points.
Under the new management of Pepa, Os Vimaranenses could be a force if they start with confidence, and we give them the edge on Sunday.
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