UEFA Champions League

AC Milan snaps 16-year semifinal drought, Real Madrid hands Chelsea latest blow

Updated Apr. 18, 2023 8:35 p.m. ET

Seven-time European champ AC Milan and current UEFA Champions League holders Real Madrid — the two most successful clubs in the competition's history — are the first two semifinalists of the 2022-23 tournament, outlasting Napoli and Chelsea Tuesday in the second legs of each respective two-game series.

After last week's 1-0 win in the opener in Milan, the Rossoneri went to Naples and beat the Serie A leaders for the third time this month. Veteran striker Olivier Giroud sealed the 2-0 aggregate win for AC Milan by scoring the game's only goal just before halftime following a breathtaking 70-yard run by Portuguese winger Rafael Leão:

In London, free-falling Chelsea lost to the 14-time titlists 2-0 on two second-half goals by Rodrygo. Real Madrid advanced 4-0 on aggregate after beating the Blues by the same 2-0 score line in the Spanish capital last week.

The other two quarterfinal matchups, Bayern Munich-Manchester City and Inter Milan-Benfica, will be decided on Wednesday, with the final four to be played next month.

Here are three quick takeaways from Tuesday's contests.

AC Milan finally back where it belongs

Italy's most glamorous club hasn't made it to the semifinals of the Champions League since 2007. That also happens to be the year AC Milan last hoisted the most coveted trophy in the club game. The Rossoneri had fallen on hard times in the interim, failing even to qualify for the event from 2015-2020.

AC Milan finally returned to the Champions League last season and, despite being eliminated in the group stage, showed that it was a squad on the come-up by winning the Scudetto last year — its first Serie A crown in more than a decade. The performances against Napoli over two legs this proves that Stefano Pioli's squad has taken another giant leap forward.

While the home team dominated the play Tuesday, AC could've put Napoli away sooner. Giroud missed two golden scoring opportunities before converting the one Leão brilliantly served him. Meantime, keeper Mike Maignan made a series of superb stops when called upon, including on Khvicha Kvaratskhelia from the penalty spot with fewer than 10 of the 180 minutes remaining

Now they're just two games away from the June 10th final in Istanbul.

And unless something remarkable happens at the San Siro on Wednesday, those two games will come against the rival they share the iconic stadium with. After topping Benfica 2-0 in Lisbon last week, it would take a monumental collapse by Simone Inzaghi's side for Inter not to advance. The two Milan teams split the season series in Serie A with both teams taking a victory, though Inter did trounce its chief nemesis 3-0 in January in the Italian Super Cup.

Still, after dispatching Napoli, AC Milan should be the favorite. What's certain is that the competition's second most decorated club is finally back where it belongs.

Things go from bad to worse for Chelsea

The mood around the Blues was surprisingly optimistic in the wake of last week's defeat in Madrid. After playing much of the second half of the first leg down a man, the two-goal deficit Chelsea took into Tuesday's decider at Stamford Bridge could've been significantly more lopsided.

Any hope that the 2021 Champions League winners could mount a comeback at home took a psychological hit when the Blues lost their third straight game under interim manager Frank Lampard over the weekend, at home, against Brighton in the Premier League. That result laid bare the fact that Chelsea, for all of the high-priced recruits it has brought in since last summer, just can't seem to function together right now.

The irony is that this latest defeat was perhaps Chelsea's best showing since Lampard returned to the sidelines. While the visitors understandably were content to sit back, protect their lead and punish Chelsea on the counter (which, to be sure, they did), the hosts also created a few clear-cut chances that, had they been finished, easily could've changed the outcome or at least made it interesting:

That's been the story of the season for Chelsea, which has managed just one goal in six games. Beating Real Madrid was always the longest of longshots for this Chelsea side. And the hard truth is that for all its resources, the Blues have no discernable direction. The club desperately needs not just a new full-time coach, but a completely revamped technical department able to determine which members of the club's bloated roster must be retained and which should be jettisoned. Until and unless that happens, missing out on next season's Champions League could go from one-off outlier to AC Milan-type drought.

Real Madrid-Manchester City all but confirmed

While AC Milan's triumph on Tuesday sets up an intriguing semifinal battle between Italian rivals from the same city, the must-see matchup will be on the other side of the bracket.

That's guaranteed even if Bayern Munich somehow overturns the 3-0 lead City ran out to last week in rain-soaked Manchester. Realistically, though, the Sky Blues are nearly certainly going to face Real Madrid in a rematch of last year’s epic semi, an 11-goal thriller from which Real advanced after extra time.

Now fronted by Erling Haaland, City looks like a group hell-bent on ensuring that the same thing doesn’t happen again this spring. Real, meantime, boasts an equally impressive squad plus the hard-won swagger of a champion. Rodrygo, Karim Benzema & Co. won’t be at all fazed by Pep Guardiola or his collection of all-planet (but still unproven) talent should they finish the job and eliminate Bayern.

If they do, two irresistible 90-minute bouts between the best two clubs in the world await.

Doug McIntyre is a soccer writer for FOX Sports. Before joining FOX Sports in 2021, he was a staff writer with ESPN and Yahoo Sports and he has covered United States men’s and women’s national teams at multiple FIFA World Cups. Follow him on Twitter @ByDougMcIntyre.