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.
Hurtig the hero after late goal sends Arsenal into Champions League quarters
Lina Hurtig's 89th minute winner ensured Arsenal progressed to the quarter-finals of the Women's Champions League after edging Juventus 1-0 on Thursday.
After being frustrated for large parts of the encounter, Hurtig bundled home from close range after Martina Lenzini's poor clearance to book the Gunners' place in the last eight.
Despite Arsenal dominating the early exchanges, it was Juventus who had the first sight of goal, though Eva Schatzer's effort was easy for Daphne van Domselaar to gather.
In a first half that saw just two shots on target, both coming from the visitors, Renee Slegers' substitutes proved to be the difference for Arsenal.
Slegers introduced Beth Mead, Stina Blackstenius and Hurtig late on, with the latter somehow putting Kim Little's cross over the bar from five yards out.
However, the Swede would atone for her earlier error, combining with fellow substitute Blackstenius to net against her former club and send them out of the competition with two group games remaining.
Meanwhile, in Group D, Barcelona edged closer to the quarter-finals of the competition with a convincing 4-1 victory over St. Polten at the Generali Arena.
The reigning champions are still three points behind Manchester City following their 2-1 win over Hammarby, and know a win against the Swedes next month will see them progress.
Kika Nazareth opened the scoring in the 20th minute after capitalising on a mistake by Kamila Dubcova, notching her second nine minutes later from close range.
Barca found themselves three goals up at the break when Vicky Lopez netted her first goal in the competition to put the result beyond doubt.
There was also a landmark moment for Alexia Putellas, who netted her 200th goal for the club with a well-taken effort into the far corner.
Valentina Madl took some of the shine off an otherwise impressive display from the visitors, who have now taken their tally to 20 goals from their four matches in the competition.
Guardiola agrees two-year contract extension with Man City
Pep Guardiola will be Manchester City manager for at least two more seasons after 2024-25, after he signed a two-year contract extension on Thursday.
The 53-year-old was coming to the end of his City deal, which was due to expire at the end of the current campaign, but he has opted to remain at the Etihad Stadium.
The deal itself will take Guardiola's tenure at the club to over a decade, making him City's longest-serving manager since Les McDowall in 1963.
There had been suggestions that he may leave at the end of the season following the announcement that director of football Txiki Begiristain was on his way out.
Guardiola was strongly linked with the England job after Gareth Southgate resigned in the wake of their Euro 2024 final defeat, but the Football Association appointed Thomas Tuchel last month.
“Manchester City means so much to me," Guardiola said. “This is my ninth season here; we have experienced so many amazing times together. I have a really special feeling for this football club.
“That is why I am so happy to be staying for another two more seasons.
“Thank you to everyone for continuing to trust and support me – The Owner, The Chairman Khaldoon, Ferran, Txiki, the players and, of course, the fans… everyone connected to Manchester City. It has always been an honour, a pleasure and a privilege to be here.
“I have said this many times before, but I have everything a manager could ever wish for, and I appreciate that so much.
“Hopefully, now we can add more trophies to the ones we have already won. That will be my focus.”
Having been appointed in 2016, Guardiola is by some distance Manchester City's most successful manager of all time, having won 18 major trophies during his time at the club.
That list includes their first-ever Champions League triumph in 2023 and six Premier League titles, including an unprecedented four on the spin.
He also boasts a 72.04% win percentage across all competitions, which is unsurprisingly the highest of any full-time City manager in history.
Shaw at the double as Man City progress in Champions League
Khadija Shaw scored twice as Manchester City beat Hammarby 2-1 to seal their place in the Women's Champions League quarter-finals.
Gareth Taylor's team entered Thursday's game with a perfect record in Group D, and their fourth win in as many European matches ensured they finished in the top two.
Shaw—the leading scorer in the Women's Super League this season with eight goals—put them ahead in the 31st minute, driving into the area after taking in Yui Hasegawa's pass before seeing her shot deflect into the top corner.
Shaw was booked for celebrating in front of the home fans despite appearing to have objects thrown at her from the stands, and Hammarby should have levelled when Julia Blakstad fired wide 10 minutes later.
The hosts did draw level three minutes into the second half as Ellen Wangerheim tapped home while City's Laura Blindkilde Brown was down appealing for a free-kick.
That parity was short-lived, though, as Shaw blasted into the top corner from 25 yards out, taking her overall tally for this season to 12 goals in all competitions.
In Group C, meanwhile, Bayern Munich lost their perfect record as they played out a 1-1 draw with Valerenga, boosting Arsenal's hopes of topping the pile.
Jovana Damnjanovic came off the bench to put Bayern ahead 15 minutes from time in Norway, but Elise Thorsnes headed home following an 88th-minute corner to snatch a point for the hosts.
Arsenal could now move within a point of Bayern when they face Juventus in Group C's other match later on Thursday.
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