Inter Milan vs AC Milan

As they face each other for a crucial Derby della Madonnina on Monday evening, Inter Milan and AC Milan will fight for Supercoppa Italiana title.

Where as Inter is looking forward for the trophy to be their fourth consecutive season winner, Milan stands to levelling the supercup eight by getting the better of their antonyms for the second time in the season.

The only three previous encounters between the two Milanese giants were in the final of the Coppa Italia back in 1977 and two Supercoppas in the recent years.

The first Milan derby in Itali’s super-cup competition was played in August 2011, and the Rossoneri triumphed 2-1; two years ago, however, the Nerazzurri inflicted a 3-0 defeat on the Rossoneri in Saudi Arabia.

The two clubs are now back in Riyadh, though the four-team format – which was first used last year – is only possible due to the fact that Inter were Italian Champions last season, and therefore qualified for the tournament ahead of Milan.

On Thursday, they overwhelmed Lombardy neighbours Atalanta BC in the first semi-final, with a second half double from Denzel Dumfries as they remained firmly on top of La Dea who have now moved within a point of them in the league both idol Napoli.

Now it is just 90 minutes to victory that would grant the Nerazzurri some sort of trophy at the expense of their city competitors and would be the perfect way to start the year that looks as very promising.

They signify an unparalleled quadruple in 2025 as the Inter is participating in the cup’s quarter finals and good in champions league apart from being in good position to defend scudetto.

The eastern trip was something Simone Inzaghi’s side embarked on in style after five successive league successes – netting more than three goals per encounter – following their win against Cagliari at the tail end of December in 2024.

The Rossoneri have progressively fallen 13 points behind since that victory at San Siro, and shortly after Christmas, they fired struggling Paulo Fonseca with Champions League qualification on the line.

As his new team defeated Juventus in Friday's second semi-final, Fonseca's fellow Portuguese coach Sergio Conceicao, whose successful tenure at Porto ended in acrimony, had some luck in his first game in the dugout.

Christian Pulisic earned and converted a penalty kick to give Milan the lead after a lackluster first half performance, and less than five minutes later, a deft deflection gave them their second goal.

That was ultimately sufficient for Conceicao to defeat a Juventus team that was supposed to include his son Francisco Conceicao, but he had to withdraw due to injury just before kickoff.

On Monday night, the former Inter player will lead Milan visiting Al-Awwal Park in an attempt to defeat his old team, marking another reunion.

Success for the red-and-black half of Italy's second city would make it a reality for Conceicao senior, but few coaches can claim to have won a trophy for their team within a week of being hired.

Marcus Thuram, Inter's top scorer, was substituted out at halftime in the team's victory over Atalanta in the semi-final, and his participation in the Supercoppa final is seriously doubtful due to a thigh injury.

Three changes from Paulo Fonseca's final lineup were made in Sergio Conceicao's first starting lineup as Milan's head coach, and that trio may be kept on Monday.

Ismael Bennacer made his first appearance after a four-month absence; Christian Pulisic also made his injury comeback and scored the equalizer; Fikayo Tomori, who had been brought up from the wilderness, began at center-back.

Mike Maignan, the goalkeeper, was named captain and will once more start behind a back four, but it's unclear who else will start for the Rossoneri.

While Tammy Abraham and Alvaro Morata were paired during the second half against Juventus, Rafael Leao might recover to play some part in the final. Conceicao has hinted that this could happen again, though he might be more careful against Inter.