Milan and Atalanta dumped out of playoffs by Feyenoord and Club Brugge | Champions League

Milan were left to rue Théo Hernandez’s sending-off following a dive as Feyenoord pegged them back on the night and advanced 2-1 on aggregate to the Champions League last 16 with a 1-1 draw in the second leg of their playoff.

Hernandez earned his second yellow card for the seven-time European champions for a dive in the 51st minute when Milan were dominating. The Italian side had cancelled out their first-leg deficit almost immediately, with forward Santiago Giménez striking against his former team in the first minute at San Siro.

From a short corner move, Christian Pulisic floated a pass towards the far post where Malick Thiaw placed a header back across goal and Giménez nodded the ball over the line. The Mexican declined to celebrate against the club he left in January, and soon after played in João Félix who put his effort over the bar.

The Feyenoord goalkeeper, Timon Wellenreuther, parried away another Félix shot and Hernandez could only hit the rebound into the side netting, while Manchester City loanee Kyle Walker drew another save with a shot from 18 yards just after the break.

Milan failed to add a second goal and the dynamic of the tie changed when Hernandez was dismissed, picking up a second yellow card for simulation. Feyenoord had struggled to make chances but only needed one, Hugo Bueno crossing for Julián Carranza to head Feyenoord level on the night and 2-1 up on aggregate.

Feyenoord held on, but defender Givairo Reed was shown a red card after the final whistle as tempers flared between the two sides. “I’m sick, still, but happy,” Carranza, who was on the bench through illness, told Ziggo Sport. “I didn’t feel great, it was something unforgettable to come in and score.”

“The way we were controlling the game in the first half and at the beginning of the second there was only one team on the pitch,” Walker told Sky Italia. “Then the referee made his decision [to send off Hernandez] and the game changed.”

Feyenoord will meet either Inter or Arsenal in the last 16, with their opponents to be decided in Friday’s draw. The result is also a boost to interim manager Pascal Bosschaart, who replaced Brian Priske two days before the first leg.

“This says about the team that they have character. I think that’s what I’m most proud of,” Bosschaart told Ziggo Sport. “You have to remember that they have received a lot of criticism, a change of coach, and then an unknown person comes in front of the group who occasionally throws in some empty slogans.”

Later on Tuesday, another Italian side crashed out of the playoffs as Atalanta were stunned 3-1 at home by Club Brugge. The Belgian side arrived in Bergamo with a 2-1 first-leg lead and extended that advantage within three minutes, Ferran Jutglà crossing for Chemsdine Talbi to fire into the bottom corner.

The 19-year-old Talbi made it 4-1 on aggregate when the Atalanta goalkeeper, Marco Carnesecchi, could only parry Christos Tzolis’s shot and he fires in the rebound. Simon Mignolet then pushed Davide Zappacosta’s shot onto the post before Brugge struck again just before the break, Jutglà finding space and finishing emphatically.

Ademola Lookman came off the bench at half-time and scored within 35 seconds, stretching his leg to steer home Zappacosta’s cross. The Europa League final hero had a chance to cut the deficit further on the hour, but his penalty was saved by Mignolet.

The hosts ran out of momentum after that, and finished with 10 men when their frustrated captain, Rafael Toloi, was shown a straight red card for a shove on Maxim De Cuyper. Club Brugge, the lowest-ranked team in the playoffs, prevailed 5-2 on aggregate and will face either Lille or Aston Villa in the last 16.

Benfica held determined Monaco to a 3-3 draw in a thrilling second leg of their playoff, securing a 4-3 aggregate win and a last-16 tie against Barcelona or Liverpool. The hosts looked comfortable after scoring in the 22nd minute, Kerem Akturkoglu’s close-range strike putting them 2-0 up on aggregate. after a fine pass from Vangelis Pavlidis.

Monaco hit back quickly, midfielder Takumi Minamino equalising with a simple finish 10 minutes later before Eliesse Ben Seghir levelled the tie on aggregate early in the second half, firing a stunning first-time shot inside the right post.

Benfica were then awarded a penalty when Monaco’s Thilo Kehrer brought down Fredrik Aursnes, and Vangelis Pavlidis coolly converted from the spot. Monaco substitute George Ilenikhena put Monaco 3-2 up on the night, but Orkun Kokcu struck two minutes later from Álvaro Carreras’ cross to restore Benfica’s overall lead.

Wednesday night will see the final four places in the last 16 decided, with Real Madrid, Dortmund and PSG taking first-leg leads into home ties against Manchester City, Sporting and Brest respectively. Juventus travel to Eindhoven with a one-goal advantage after winning 2-1 in Turin last week.