Juventus suffered another disappointing exit from the Champions League on Wednesday, joining other Italian clubs in failing to make it past lower-ranked teams in the playoffs.

The two-time European champions lost 3-1 after extra time to PSV Eindhoven, who advanced to the round of 16 with a 4-3 aggregate score. Juventus had briefly taken the lead in the second half thanks to a powerful shot from U.S. wing-back Timothy Weah in the 63rd minute, which made the score 1-1 and gave the Bianconeri a 3-2 advantage. However, they were ultimately outlasted by their Dutch opponents.

The previous night also saw AC Milan and Atalanta eliminated at home by Feyenoord and Club Brugge, respectively.

Out of the five Italian teams that entered the new 36-team Champions League format, Bologna failed to even reach the knockout stage in their first appearance in 60 years. Inter Milan is the only Serie A team left standing, advancing to the round of 16 for the upcoming draw on Friday.

Ivan Perišić, a former Inter Milan star, played a key role in eliminating Juventus from the competition on Wednesday. The 36-year-old Croatian veteran gave PSV the lead in the 53rd minute, expertly controlling a precise cross from Noa Lang before firing a shot past Juventus goalkeeper Michele Di Gregorio.

Timothy Weah brought Juventus back into the game with a powerful 20-yard shot, which was initially ruled offside. However, after a two-minute video review, the decision was overturned, and the goal was awarded.

PSV’s Ismael Saibari equalized the aggregate score in the 74th minute, and the decisive goal came in the 98th minute from defender Ryan Flamingo. Flamingo capitalized on a loose ball in the goalmouth after a low cross from Belgium winger Johan Bakayoko deflected off Juventus defender Federico Gatti and goalkeeper Michele Di Gregorio.

In the upcoming round of 16 draw on Friday, PSV will face either Arsenal or Inter Milan, two of Perišić’s former clubs still in the competition. Brugge, another of Perišić’s former teams, will enter the draw as the lowest-ranked team according to UEFA, representing Belgium, the lowest-ranked nation still in the tournament.

With three Italian teams now eliminated, Italy’s chances of securing a fifth entry into the Champions League next season — a reward given to the countries with the best collective results in European competitions — seem slim.

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