The last time Milan punched its ticket to the Champions League quarterfinals was the 2011/12 season. In that time, which spans over a decade, Milan went through struggles that saw the historic club finish 10th in Serie A. However, last season’s Scudetto winners are remedying the wounds with impressive performances against elite European opposition.

This time, it was a gutsy scoreless draw on the road at Tottenham Hotspur. Following a 1-0 win at San Siro, Milan used similar tactics to starve Spurs of any true threats on goal. Then, a careless and frankly silly second yellow card offense from Cristian Romero made the one-goal mountain that much steeper for Antonio Conte’s side. Despite the Italian’s return to the touchline, Tottenham were devoid of offensive opportunities, perhaps a credit to Milan’s defense.

Traditionally, in a scoreless draw where one team advances, the applause goes to the goalkeeper. Mike Maignan made saves, yes. However, the attempts Spurs had were tame for the most part. It took desperation in stoppage time for Spurs to truly test the Frenchman. Son Heung-min whipped a free kick in and Harry Kane met it with his head. Maignan instinctively got down to his right to claw the ball away from the goal line.

While there was still around five minutes left in stoppage time, Spurs got no better looks. If anything, Milan almost put the tie to bed soon after Kane’s near miss. Regardless, the scoreless draw was was enough to send Milan through on aggregate, stemming from a Brahim Diaz goal in the first leg.

Milan back in Champions League quarterfinals, Spurs trophyless again

To many, Milan was a surprise winner of Serie A a season ago. Inter looked poised to defend its crown while Napoli continued building and Juventus reeled. Milan under Stefano Pioli did enough to win the Scudetto for the 19th time, level with Inter for second in history.

However, Milan truly has its history built in the UEFA Champions League. Therefore, the performance from Milan to get back into the quarterfinals of the Champions League is where many supporters of the Rossoneri believe they belong. After all, Milan’s seven titles are the second-most all time by a club.

For Spurs, the trophy cabinet is not as glittering. Now, elimination in the round of 16 leaves Harry Kane and Son Heung-min trophyless again. The last time Spurs won a major trophy was back in the 2007/08 League Cup.

This loss brings even more questions to the future of some of the key names at Tottenham. Antonio Conte is out of a contract at the conclusion of this season. Consequently, he has at most 12 games remaining on his current contract, all part of the Premier League after FA Cup elimination recently. Harry Kane may be more inclined to leave after another disappointing conclusion to the season.

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