It's cup specialist vs. serial runner-up as Milan takes on Bologna in the Italian Cup final

MILAN (AP) — A cup specialist will take on a serial runner-up when AC Milan plays Bologna in the Italian Cup final on Wednesday.

And both teams will be looking to get their hands on the trophy for the first time in decades.

Bologna hasn’t won the Italian Cup since 1974, which was its last major trophy.

Milan has won plenty of trophies since then, but last lifted the Italian Cup 22 years ago — losing two finals in the intervening years.

This time, however, the Rossoneri are led by a cup specialist in coach Sérgio Conceição.

Indeed, Conceição has already steered Milan to a trophy this season — winning the Italian Super Cup in January just a week after being appointed as coach.

That was the 50-year-old’s 12th trophy as coach, with nine coming in cup competitions.

Conceição also lifted seven cup trophies as a player, with Porto and Lazio.

However, even if Milan ends the season with two trophies in Conceição’s five months in charge, it might not be enough to save the Portuguese coach’s job.

Milan is eighth in Serie A with two rounds remaining and only has a slim chance of qualifying for the Champions League — or any European competition.

Winning the Italian Cup would earn Milan a spot in the Europa League and go some way toward salvaging a season where the Rossoneri were never competitive in Serie A or Europe, having been dumped out of the Champions League by Feyenoord in the knockout playoff round.

“It’s not the moment to talk about my future,” Conceição said. “Now we’re only thinking about this final, against a difficult team to face.

“I have my character and my personality, I’ve changed things and you need time but at Milan you don’t have time. … At Milan, what counts is winning trophies and Wednesday we have a great chance.”

In contrast to Conceição, Bologna coach Vincenzo Italiano has not fared well in finals.

Italiano never won a cup in his playing days and, as Fiorentina coach, he lost back-to-back Europa Conference League finals — in 2023 and 2024 — and finished runner-up in the 2023 Italian Cup.

The cup final in Rome will be the teams' second meeting in less than a week.

Two goals from Santiago Giménez, either side of a Christian Pulisic strike, saw Milan rally to beat Bologna 3-1 and seriously dent its opponent’s chances of qualifying for the Champions League again.

“We were ahead and we thought we could control it, Milan didn’t give the impression of wanting to attack,” Bologna scorer Riccardo Orsolini said in an interview with Italian newspaper Corriere della Sera.

“We gave them the spark that rekindled them and we got sliced through like butter. If we play like that in Rome we’ll get slapped. We’ve understood what we shouldn’t do.”

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Bologna's Riccardo Orsolini celebrates after scoring during the Serie A soccer match between Milan and Bologna at San Siro Stadium in Milan, Italy, Friday May 9, 2025. (Spada/LaPresse via AP)

AC Milan's Santiago Gimenez celebrates after scoring their first goal during the Serie A soccer match between Milan and Bologna at San Siro Stadium in Milan, Italy, Friday May 9, 2025. (Spada/LaPresse via AP)

AC Milan's Christian Pulisic celebrates after scoring their second goal of the game during the Serie A soccer match between Milan and Bologna at San Siro Stadium in Milan, Italy, Friday May 9, 2025. (Spada/LaPresse via AP)

Bologna's head coach Vincenzo Italiano shouts instructions to his players during the Italian Serie A soccer match between Bologna FC 1909 and Juventus FC at Renato Dall'Ara Stadium, in Bologna, Italy, Sunday, May 4, 2025. (Massimo Paolone/LaPresse via AP)

AC Milan's head coach Sergio Conceicao reacts during the Serie A soccer match between Milan and Bologna at San Siro Stadium in Milan, Italy, Friday May 9, 2025. (Spada/LaPresse via AP)

DUBAI, United Arab Emirates (AP) — U.S. President Donald Trump said Iran wants to negotiate with Washington after his threat to strike the Islamic Republic over its bloody crackdown on protesters, a move coming as activists said Monday the death toll in the nationwide demonstrations rose to at least 544.

Iran had no immediate reaction to the news, which came after the foreign minister of Oman — long an interlocutor between Washington and Tehran — traveled to Iran this weekend. It also remains unclear just what Iran could promise, particularly as Trump has set strict demands over its nuclear program and its ballistic missile arsenal, which Tehran insists is crucial for its national defense.

Meanwhile Monday, Iran called for pro-government demonstrators to head to the streets in support of the theocracy, a show of force after days of protests directly challenging the rule of 86-year-old Supreme Leader Ayatollah Ali Khamenei. Iranian state television aired chants from the crowd, who shouted “Death to America!” and “Death to Israel!”

Trump and his national security team have been weighing a range of potential responses against Iran including cyberattacks and direct strikes by the U.S. or Israel, according to two people familiar with internal White House discussions who were not authorized to comment publicly and spoke on condition of anonymity.

“The military is looking at it, and we’re looking at some very strong options,” Trump told reporters on Air Force One on Sunday night. Asked about Iran’s threats of retaliation, he said: “If they do that, we will hit them at levels that they’ve never been hit before.”

Trump said that his administration was in talks to set up a meeting with Tehran, but cautioned that he may have to act first as reports of the death toll in Iran mount and the government continues to arrest protesters.

“I think they’re tired of being beat up by the United States,” Trump said. “Iran wants to negotiate.”

He added: “The meeting is being set up, but we may have to act because of what’s happening before the meeting. But a meeting is being set up. Iran called, they want to negotiate.”

Iran through country's parliamentary speaker warned Sunday that the U.S. military and Israel would be “legitimate targets” if America uses force to protect demonstrators.

More than 10,600 people also have been detained over the two weeks of protests, said the U.S.-based Human Rights Activists News Agency, which has been accurate in previous unrest in recent years and gave the death toll. It relies on supporters in Iran crosschecking information. It said 496 of the dead were protesters and 48 were with security forces.

With the internet down in Iran and phone lines cut off, gauging the demonstrations from abroad has grown more difficult. The Associated Press has been unable to independently assess the toll. Iran’s government has not offered overall casualty figures.

Those abroad fear the information blackout is emboldening hard-liners within Iran’s security services to launch a bloody crackdown. Protesters flooded the streets in the country’s capital and its second-largest city on Saturday night into Sunday morning. Online videos purported to show more demonstrations Sunday night into Monday, with a Tehran official acknowledging them in state media.

In Tehran, a witness told the AP that the streets of the capital empty at the sunset call to prayers each night. By the Isha, or nighttime prayer, the streets are deserted.

Part of that stems from the fear of getting caught in the crackdown. Police sent the public a text message that warned: “Given the presence of terrorist groups and armed individuals in some gatherings last night and their plans to cause death, and the firm decision to not tolerate any appeasement and to deal decisively with the rioters, families are strongly advised to take care of their youth and teenagers.”

Another text, which claimed to come from the intelligence arm of the paramilitary Revolutionary Guard, also directly warned people not to take part in demonstrations.

“Dear parents, in view of the enemy’s plan to increase the level of naked violence and the decision to kill people, ... refrain from being on the streets and gathering in places involved in violence, and inform your children about the consequences of cooperating with terrorist mercenaries, which is an example of treason against the country,” the text warned.

The witness spoke to the AP on condition of anonymity due to the ongoing crackdown.

The demonstrations began Dec. 28 over the collapse of the Iranian rial currency, which trades at over 1.4 million to $1, as the country’s economy is squeezed by international sanctions in part levied over its nuclear program. The protests intensified and grew into calls directly challenging Iran’s theocracy.

Nikhinson reported from aboard Air Force One.

In this frame grab from video obtained by the AP outside Iran, a masked demonstrator holds a picture of Iran's Crown Prince Reza Pahlavi during a protest in Tehran, Iran, Friday, January. 9, 2026. (UGC via AP)

In this frame grab from footage circulating on social media from Iran shows protesters taking to the streets despite an intensifying crackdown as the Islamic Republic remains cut off from the rest of the world in Tehran, Iran, Friday, Jan. 9, 2026.(UGC via AP)

In this frame grab from footage circulating on social media from Iran showed protesters once again taking to the streets of Tehran despite an intensifying crackdown as the Islamic Republic remains cut off from the rest of the world in Tehran, Iran, Saturday Jan. 10, 2026. (UGC via AP)