Preview: Tottenham Hotspur vs. AC Milan 

Preview: Tottenham Hotspur vs. AC Milan 

Seeking to overturn a one-goal deficit upon Antonio Conte’s return to the dugout, Tottenham Hotspur host AC Milan in the second leg of their Champions League last-16 tie on Wednesday evening.

An early Brahim Diaz goal sealed a 1-0 win for the Rossoneri in the first leg three weeks ago, but both clubs enter the midweek reunion on the back of lowly domestic defeats.

A brief return to the touchline for the gallbladder-less Conte could hardly have gone worse for the Italian, whose side were humbled 4-1 by Leicester City before Diaz’s seventh-minute strike saw Milan glean a narrow advantage in the first leg of their Champions League last-16 tie on February 14.

While experiencing a miserable return to San Siro, a flight back to his homeland was timely for Conte, who once again passed the torch over to Cristian Stellini in order to continue his recovery from surgery, but the ex-Inter Milan boss is now poised to make his second comeback with his side in dire need of inspiration.

Three days after bowing out of the FA Cup to second-tier Sheffield United – losing in the fifth round for the fourth season running – a silverware-starved Spurs succumbed to another 1-0 away defeat in the Premier League, this time at Wolverhampton Wanderers courtesy of Adama Traore’s second-half winner.

Still fourth in the table – albeit looking over their shoulder as Liverpool creep up on them – Tottenham are at risk of a third last-16 elimination from their last four runs in the top tier of European football, although they have managed to progress from two of their last three continental ties when losing the first leg.

A three-game winning run at the Tottenham Hotspur Stadium – during which time they have prevented Manchester City, Chelsea and West Ham United from scoring – is also cause for optimism, and Milan hardly enter the second leg brimming with unbridled confidence either.

Having weathered a Tottenham storm after Diaz reacted quickest to propel them into the ascendancy, Milan are just 90 minutes away from reaching the Champions League quarter-finals for the first time since the 2011-12 campaign, but restoring the glory days of the Rossoneri is a box that remains unticked on Stefano Pioli’s CV.

Victory over Spurs marked the second of a four-game winning run across all tournaments for Milan, who also kept clean sheets in Serie A wins over Torino, Monza and Atalanta BC in February, but a trip to Artemio Franchi to face Fiorentina at the weekend ended in despair.

Nicolas Gonzalez’s penalty and Luka Jovic’s header stunned the Rossoneri before Theo Hernandez came up with a last-gasp consolation, but with Napoli still riding off into the sunset, the league is ostensibly a foregone conclusion for the fifth-placed Scudetto holders, who are a whopping 19 points adrift of their Naples counterparts.

As such, the Champions League represents the Rossoneri’s last realistic chance to add to their trophy cabinet this season, but a meagre record of just two wins from their last eight away from home will do them no favours in that regard, and only two of their six Champions League games away from home since 2021 have ended in victory.

On a brigher note for Milan, they have suffered just three eliminations from their last 21 Champions League knockout battles when prevailing in the first leg, but they have been outscored 9-1 in their last three trips to the English capital, and keeping an unfancied shot at Champions League glory alive would certainly quell some of the familiar fury circling around the Tottenham Hotspur Stadium for the ever-inconsistent Lilywhites.

Tottenham Hotspur Champions League form:

Tottenham Hotspur form (all competitions):

AC Milan Champions League form:

AC Milan form (all competitions):

We say: Tottenham Hotspur 1-1 AC Milan (Milan win 2-1 on aggregate)
Home comforts will no doubt benefit Spurs’ chances of turning the tie on its head, but Conte is facing a thankless task to rally his profligate troops after a pair of demoralising domestic defeats.

Milan’s recent spate of underwhelming road performances could see the Scudetto-holders tread with caution too, but with a well-rested Leao returning to a near fully-fit squad, the Rossoneri can hold out for the draw which would seal their spot in the last eight, as Tottenham’s dreams of silverware crash and burn for another year.

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