For the first time in nearly a decade, AC Milan will participate in the knockout stages of the Champions League when they host Tottenham at the San Siro on Tuesday. The Rossoneri haven’t been part of the Round of 16 since losing to Atletico Madrid in the 2013-14 season, and now have an opportunity to make a run in the final season at their iconic stadium.
To do so, they will need to do something they’ve failed to do in their four other meetings with Tottenham – get a victory. Spurs have never lost to their Italian counterparts, but they’re licking their wounds following a 4-1 defeat to Leicester at the weekend.
AC Milan took a step towards their first Champions League quarter-final appearance for 11 years as Brahim Diaz’s goal gave the Italians a 1-0 win over Tottenham Hotspur in their last-16 first leg at the San Siro on Tuesday.
The Spaniard headed in a rebound in the seventh minute after a superb double save by Tottenham’s second-choice keeper Fraser Forster and the seven-time winners kept the Londoners at bay.
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Spurs, weakened by injuries and suspensions, responded positively in the first half to dominate possession but were unable to seriously worry the hosts.
Milan should have increased their advantage after the break with substitutes Charles De Ketelaere and defender Malick Thiaw both wasting glorious headed chances.
Tottenham sent on Brazil forward Richarlison for the last 20 minutes and, while they were unable to avoid a first-ever defeat by Milan, they will head home still hopeful of turning the tie around and reaching the last eight.
“It wasn’t hard to prepare this game tactically, with all the duels, but I am very happy with how my players performed,” Milan coach Stefano Pioli said.
“We could have scored a second goal — we had some clear chances. I am happy with the performance but it’s only the first leg and the next game will be surely more difficult.”
Milan’s record against Premier League clubs has been lamentable in recent years with only one win in 17 ahead of their clash with Antonio Conte’s Spurs side.
But faced with inconsistent opponents who were without the suspended Pierre-Emile Hojbjerg and injured Rodrigo Bentancur in midfield and sidelined goalkeeper Hugo Lloris they deservedly ended that run with a tenacious display.
AC Milan vs Tottenham picks and predictions
AC Milan finally ended their freefall on Friday with a 1-0 win over Torino. Their first clean sheet since before the World Cup was critical, as they ended a winless run of seven matches that saw them lose five times. During that time, they slid from second in the Serie A table down to fifth, and now sit 18 points adrift and outside the Top 4.
Manager Stefano Pioli is still under fire after watching his team slip down the Serie A table with a nosedive that began when they conceded two late goals to blow a 2-0 lead over Roma. They’ve been eliminated from the Coppa Italia during the slide as well, leaving the Champions League as their last remaining hope for silverware.
Captain and starting keeper Hugo Lloris is also sidelined, and backup Fraser Forster was left looking foolish at the weekend as he missed saves he should’ve made — although his defense didn’t help him much.
Milan are dealing with injury issues of their own, especially in goal. Mike Maignan, who had one of the best goals allowed below xG ratings in all of Europe a season ago, continues to be sidelined but isn’t far from returning. Defender Allesandro Florenzi is also absent.
What these teams do have are strikers capable of delivering if given a moment of opportunity. Harry Kane and Olivier Giroud are lethal finishers, and Heung-min Son and Rafael Leao both offer strong options from their respective left flanks.
That’s why your best play in this contest is to stay away from a result, and instead take both teams to score. Tottenham’s back line will be heavily tested without their protection, and Milan’s been leaking goals for the past six weeks. This should be a cagey affair, but one where both teams find themselves on the scoresheet before it’s all over.
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