Inter Milan conceded twice in the last eight minutes of extra-time as their grip on the Coppa Italia came to an end with a 2-1 defeat to Bologna.
Lautaro Martinez had a penalty saved as normal time ended goalless, before Carlos Augusto headed hosts Inter into a 92nd-minute lead.
But Sam Beukema and Dan Ndoye struck in a dramatic turnaround as the back-to-back cup winners were dumped out at the quarter-final stage for the first time since the 2018-19 season.
Inter’s Marko Arnautovic tried his luck from range but his sixth-minute effort went wide in a cagey start.
Bologna responded with a chance of their own in the 18th minute when Giovanni Fabbian’s shot grazed the outside of the post.
Inter pushed for an opening but were being held off by a stubborn Bologna.
The closest they got in the first half was when Davide Frattesi went down under a challenge but his penalty appeals were waved off.
Inter came out fast after the break and came close in the 49th minute through the dangerous Fratessi.
The goalscoring midfielder lost his marker and met Alessandro Bastoni’s cross, but he failed to connect with the ball properly.
Simone Inzaghi’s side had kept four successive clean sheets prior to this match and their quality showed as their tight back three and hard working midfield stifled any Bologna attack.
But at the other end Martinez missed a golden opportunity to give Inter the lead in the 65th minute.
Bologna’s Tommaso Corazza was deemed to have handled the ball in the box following a corner but Martinez’s placed effort was saved by Federico Ravaglia.
The striker had scored 17 in all competitions up to that point and failed to add to his tally as Inter’s frustrations grew.
The Argentina international was keen to make up for his miss when he drove with the ball before shooting from range, but his shot sailed just over the Bologna crossbar.
The stalemate remained at full-time, but Inter finally broke the deadlock just two minutes into extra-time.
Federico Dimarco’s corner picked out Augusto who rose highest and nodded his effort home.
But the visitors responded eight minutes from time when Joshua Zirkzee flicked on a corner to the charging Beukema who smashed home from close range to make it 1-1.
And Bologna grabbed another in the 116th minute.
Zirkzee produced another moment of brilliance to beat his man in midfield before he threaded a pass through to Ndoye, who casually chipped Emil Audero to give his side a 2-1 win.
Liverpool 1-0 Real Betis: Szoboszlai gets Slot era up and running
Dominik Szoboszlai's goal was the difference as Arne Slot's first game in charge of Liverpool with spectators present ended in a 1-0 win over Real Betis in Pittsburgh.
Liverpool lost 1-0 in a behind-closed-doors meeting with Preston North End last week, but they were victors in sweltering conditions when their pre-season tour of the United States got under way on Friday.
Szoboszlai scored the only goal after 34 minutes, stroking his finish past Adrian after Mohamed Salah slipped a pass through to the Hungary international.
That goal came four minutes after Curtis Jones was forced off through injury, being replaced by 17-year-old Trey Nyoni.
Former Reds goalkeeper Adrian denied Conor Bradley as a strong Liverpool side chased a second, while Harvey Elliott nodded wide from a Kostas Tsimikas cross.
After Slot rang the changes with 63 minutes gone, Kaide Gordon missed Liverpool's best chance to make it 2-0 by dragging his effort wide, but it did not matter as a controlled performance saw the Reds home.
Data Debrief: Reds in cruise control
Slot had been expected to bring a slightly more measured approach than the "heavy metal football" preached by his predecessor Jurgen Klopp, and that was on full display on Friday as Betis were held at arm's length.
Liverpool enjoyed 62.7% of the possession throughout the match, though Slot will be looking for more penetration when they face Arsenal in the next game of their tour on Wednesday, having only recorded 12 touches in the penalty area to Betis' 10.
Sessegnon rejoins boyhood club Fulham after Tottenham departure
Ryan Sessegnon has resigned for Fulham on a free transfer, five years after leaving the club.
The 24-year-old signed a two-year contract with the Cottagers with the option to extend for a further year following his departure from Tottenham last month.
In his first spell at the club, Sessegnon worked his way through the academy over 11 years, scoring 25 goals in 120 first-team appearances.
He then moved to Spurs in a £25million deal in 2019, though struggled to nail down a place in North London, making just 57 appearances in all competitions, and scoring three goals.
"It's amazing to be back. Emotional, as well," he told FFCtv. "It's where it started for me, where everything began, and it's amazing to be back.
"It will always be home for me. I think it had the feeling that it was meant to be, coming back here, so I'm delighted to get it done."
Sessegnon is Fulham's first signing of the transfer window, though they have seen plenty of first-team departures already, with Joao Palhinha, Tosin Adarabioyo and Bobby De Cordova-Reid all leaving the club.
Dewsbury-Hall: Maresca will surprise people at Chelsea
Kiernan Dewsbury-Hall believes new Chelsea manager Enzo Maresca will "surprise a lot of people" when they watch the Blues this season.
The Italian led Leicester City straight back to the Premier League as Championship winners in his only season in charge and succeeds Mauricio Pochettino at Stamford Bridge.
The Foxes topped the second division table with 98 points, with Dewsbury-Hall a key figure in his squad as he netted 12 goals and provided 14 assists last season – his best tally in a single campaign.
Dewsbury-Hall was also named Leicester's Player and Players' Player of the Year.
The midfielder made the switch to West London earlier this month for £30million and is confident that Maresca will have Chelsea challenging for trophies in no time.
"The manager was a big catalyst in wanting me to come," Dewsbury-Hall told BBC Sport.
"I knew from Leicester, a club that went down and had a lot of problems, how he managed to galvanise that if everyone manages to buy into the system.
"I genuinely think in a short space of time we can be pushing for minimum top four - but more than that.
"He may be unknown for a lot of people, but he is top, top level. He will surprise a lot of people."
Chelsea's pre-season got off to a frustrating start as they were held to a 2-2 draw by League One side Wrexham in Maresca's first game in charge on Wednesday.
Dewsbury-Hall did not play in that match but is training with the squad in the United States and could feature in their next outing against Celtic on Saturday.
The 25-year-old is confident the manager's tactics will come across soon, with the players buying into his style.
"We've only been doing it for two or three weeks, but the combination plays are really quick and tidy," he added.
"That's after two weeks. I remember he said to us at Leicester after six months or a year, there might be teething problems at the start, but it will improve.
"Within the first week at Leicester, I was convinced this was top, top level. I felt a bit stupid; I thought I knew a lot about football, but he was teaching me things on a daily basis that I didn't really know before. He has an aura, he can be strict, or gentle and soft - he has both sides.
"I am getting the same feedback here with the lads. They've bought into it here from minute one which is exciting. With a system and philosophy, you need everyone to buy in because, if they do, you can really achieve something."
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