The Primeira Liga champions will taken on the Taca de Portugal winners when Benfica meet Sporting Lisbon in the Portuguese Super Cup at the Estadio Municipal de Aveiro on Sunday.
After winning the league title ahead of Porto, Jesus ended his reign as Benfica boss to make the switch to Sporting and all eyes will be on the veteran coach this weekend.
Benfica
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In what turned out to be one of the most exciting finishes to a Portuguese season in recent memory, Benfica held their nerve over the closing stages of the campaign to finish three points clear of Porto and nine points ahead of Sporting.
It would prove to be the final celebration for Jesus, who left the club shortly after due to a breakdown in contract negotiations, but a change in coach would prove to be just the beginning of a busy summer for the Portuguese champions, with key figures Maxi Pereira and Ivan Cavaleiro among the players to leave, for Porto and Monaco respectively.
Rui Vitoria has been unable to dip into the transfer market in the same way his predecessors had done, but with time still remaining in the window, the new Benfica boss will be hopeful of boosting his squad after watching their rivals strengthen over the last couple of months.
Earning his reputation as an impressive young coach who led Vitoria de Guimaraes to fifth spot last season, Vitoria will be fully aware that he is under the spotlight more than ever as he looks to handle the pressure of defending the title and producing an acceptable Champions League campaign.
Despite a lack of investment, there was good news for Vitoria and the Benfica fans this week as they completed a deal to take Greek strike Kostas Mitroglou on loan from Fulham, but it remains to be seen whether he can regain his best form in Portugal.
There is no doubt that Vitoria will be judged on success in the league and the performances in Europe, but the fans will be wary of anything less than a win this weekend as Benfica look to prove that they are still the team to beat, especially after a pre-season which saw them win just one game in a penalty shootout.
Pre-season form: LLLWL
Sporting
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After falling behind the top two in the title race last season, it would be fair to say that Sporting's fans wanted immediate change, and the club's hierarchy were quick to steal the headlines when they announced the appointment of Jesus just days after he had officially left Benfica.
An 11-game unbeaten run at the end of the season may have been enough to save Marco Silva in a different situation, who watched his side produce some impressive displays at home and in Europe, but with the pressure on the club to steer themselves back to contention, it is difficult to argue with the decision to appoint Jesus.
Never one to avoid the limelight, Jesus will be the centre of attention at the weekend as he looks to inflict defeat on the club where he won eight major honours, but delivering Sporting their first title since 2002 will be his biggest test as a manager.
Despite no points being on offer on Sunday, the Sporting boss and the club's fans will be keen to put down a marker for the rest of the season as they bid to win the first trophy on offer and prove to both Benfica and Porto that they have the squad capable of a strong challenge.
A meeting with a rival, no matter what the occasion, will catch the attention, but Jesus is sure to have on eye on the two-legged meeting with CSKA Moscow, too, as he looks to take Sporting into the group stages of the Champions League once again.
Sporting's transfer business has been quietly impressive this summer, with Joao Pereira making his return to Portugal and the immensely talented, but inconsistent, Bryan Ruiz joining from Fulham before the signing of Alberto Aquilani was confirmed on Friday.
Bigger challenges await the cup winners, but Jesus can boost the confidence in the dressing room and in the stands by leading Sporting to a win over his former employers.
Pre-season form: DWW
Team News
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Ruiz has already managed to impress in a Sporting shirt after helping them to a 2-0 victory over Roma in their final pre-season friendly, and the Costa Rican is likely to start on the right of a 4-4-2 formation.
Islam Slimani should partner Teofilo Gutierrez in attack, while Naldo is expected to start alongside Paulo Oliveira at the back.
Mitroglou is unlikely to be used by Vitoria after only signing his loan deal on Friday, but Nicolas Gaitan is set to start for Benfica, despite the speculation that continues to surround the attacking midfielder's future.
The biggest question mark about the side could be in midfield, with Joao Teixeira likely to earn a start ahead of Pizzi, who has been a regular in pre-season.
Benfica possible starting lineup:
Cesar, Silvio, Luisao, Jardel, Eliseu, Teixeira, Samaris, Gaitan, Talisca, Lima, Jonas
Sporting possible starting lineup:
Patricio, Pereira, Naldo, Oliveira, Jefferson, Adrien, Mario, Ruiz, Carrillo, Slimani, Gutierrez
Head To Head
Sporting managed to hold the champions to a 1-1 draw in both of their meetings last season, but there is no doubt that Benfica have dominated the rivalry in recent years thanks to a seven-game unbeaten run in competitive games.
One win in the last 16 meetings between the two sides makes for difficult reading for all Sporting supporters, while Benfica fans will be happy to learn that their side have scored in all but one of the last 14 clashes.
We say: Benfica 1-2 Sporting
Despite the changes which have taken place at Benfica since their title win they remain a very strong side, but their form in pre-season should not be ignored and it appears that they might not yet be ready for the start of the season. Sporting are likely to be positive against the champions and Jesus could be rewarded against his former side.
Callum Mulvihill
