Champions League: 10-man AC Milan eliminated, Club Brugge completes shocker

Doug McIntyre

Soccer Journalist

Bayern Munich, Benfica, Club Brugge and Feyenoord all advanced on Tuesday to the UEFA Champions League round of 16, with the final four spots to be determined on Wednesday.

Here are the biggest takeaways from Tuesday’s four decisive knockout phase playoff second legs.

Hernández’s silly red card dooms AC Milan

The seven-time European champions were forced to settle for a 1-1 tie on Tuesday with Dutch club Feyenoord after French star Theo Hernández was shown a red card early in the second half. Milan — which started U.S. men’s national team standouts Christian Pulisic and Yunus Musah on Tuesday — dropped the opening game of the two-match, total-goals-wins home-and home series 1-0 last week in the Netherlands. With a 2-1 win on aggregate, Feyenoord advanced to the round of 16.

All was well for the Rossoneri during the second leg at the San Siro when Pulisic helped set up Mexican national teamer (and former Feyenoord forward) Santiago Giménez, who put Milan up 1-0 less than a minute into the match. But Argentine striker Julián Carranza, who joined Feyenoord from the Philadelphia Union of MLS last summer, came off the bench in the second half and pulled the visitors level 22 minutes after Hernandez’s dismissal had reduced the hosts to 10 men.

AC Milan had utterly dominated the contest during the opening 51 minutes. That changed when Hernandez received his second caution, for diving, and his walking papers. The hosts mounted a furious late comeback attempt but couldn’t find the goal they needed to send the match to extra time.

It’s a hugely disappointing end to the Champions League campaign for Milan, which had been heavily favored to advance. Instead, they’ll sit out the round of 16 for the second consecutive year and the ninth time in 10 seasons.

Feyenoord, on the other hand, can celebrate a famous triumph. The 1970 European titlist is back in the last 16 of the world’s top club competition since 1993-94. They’ll play Arsenal or Inter Milan next.

Heartbreak for Celtic as Bayern Munich snares late winner

For more than 90 minutes in Munich, Celtic’s USMNT center back duo of Cameron Carter-Vickers and Auston Trusty kept one of the most dangerous attacks in the global game from scoring in front of their own fans.

That looked to be enough as the clock ticked well into second half stoppage time, with the Glasgow giants on the verge of a 1-0 win thanks to German winger (and former Bayern youth prospect) Nicolas-Gerrit Kühn that would send the teams to half an hour of extra time tied 2-2 on aggregate.

The visitors never got there. Following a Kasper Schmeichel save with just seconds remaining, Carter-Vickers attempted to clear the rebound off his own goal line before the hosts’ Alphonso Davies could poke home the equalizer. Unfortunately for the American, he blasted his effort off of Davies and into his own net:

It was a cruel way to end Celtic’s Champions League campaign, but the Scottish champs should be proud after giving a perennial trophy contender everything it could handle over the two legs. There’s also a silver lining for Carter-Vickers and Trusty. The pair certainly didn’t hurt their stock this month in the eyes of U.S. coach Mauricio Pochettino, who could name both to his roster for the USMNT’s March 20 Concacaf Nations League quarterfinal against Panama.

Meantime, Bayern will meet Atlético Madrid or Bundesliga rival Bayern Leverkusen in the last 16.

Benfica and Club Brugge finish the job

The most surprising first leg result of these playoffs was undoubtedly Club Brugge’s 2-1 win over Atalanta. Yet the Italian side had everything to play for at home on Tuesday. An early goal would’ve put them right back into the fray.

The early goal came, all right — for the visitors. Chemsdine Talbi then added his second midway through the first half to stun the crowd at Stadio Atleti Azzurri d’Italia in Bergamo, before Ferran Jutglà made it 3-0 with a rocket of a shot just before the break.

Ademola Lookman pulled one back for Atalanta soon after the teams returned to the field, but a penalty stop by former Liverpool keeper Simon Mignolet later on ensured that that was as close as the Serie A side got. The Belgians will face either Aston Villa or Lille in the next round.

In Portugal, Monaco stormed back from two separate one-goal deficits to pull level on aggregate through an 81st-minute strike by Nigerian sub George Ilenikhena. But the goal they conceded in last week’s 1-0 defeat at home came back to haunt them, as midfielder Orkun Kökçü answered almost right away to send Benfica back to the business end of the tournament.

The Eagles will face a far sterner test next, though, against five-time winner Barcelona or top-seeded Liverpool.

The full round of 16 draw will be revealed on Friday.

Doug McIntyre is a soccer writer for FOX Sports who has covered the United States men’s and women’s national teams at FIFA World Cups on five continents. Follow him at @ByDougMcIntyre.