Match coverage

Milan 1-0 Tottenham: Diaz’s early opener stings Spurs as Champions League knockout stages return

Brahim Diaz of Ac Milan celebrates after scoring his team's first goal during the UEFA Champions League round of 16 leg one match between AC Milan...

Milan playmaker Brahim Diaz scored his first goal since October – a rebounded finish from close-range – as Antonio Conte’s Tottenham side suffered consecutive defeats for the second time already in 2023 with a frustrating collective showing in the first leg of their Champions League last-16 tie. The return fixture might be in three weeks’ time, but they’ll have to execute with far more incision than they managed here if they’re to advance into the quarter-finals.

Milan hold gritty first leg advantage vs. stifled spurs display

Malick Thiaw of AC Milan and Dejan Kulusevski of Tottenham Hotspur compete for the ball during the UEFA Champions League round of 16 leg one match...
Malick Thiaw (right) kept Dejan Kulusevski quiet and could’ve added to Milan’s slender lead, late on
  • Midfield duo Oliver Skipp and Pape Matar Sarr in Tottenham’s starting XI after serious injuries to Rodrigo Bentancur and Yves Bissouma, Pierre-Emile Hojbjerg suspended
  • Meanwhile, first-choice goalkeeper Mike Maignan (calf), centre-back Fikayo Tomori (hip) and midfielder Ismael Bennacer (thigh) among key players all sidelined for Milan
  • Eric Dier’s second-half booking means he’ll miss the return leg in north London on March 8, more unwelcome news for Antonio Conte’s unpredictable Tottenham side

While Antonio Conte recovered from gallbladder surgery, his assistant manager Cristian Stellini took charge as Tottenham suckerpunched defending champions Manchester City on February 5.

Harry Kane, who that day surpassed Jimmy Greaves as the club’s new record top goalscorer on 267 goals, was congratulated over the phone in the dressing room by Conte afterwards. “Thanks and boss, see you Wednesday?” was the hopeful finishing line Kane delivered to the Italian.

It was his tongue-in-cheek way of speaking into existence a chance for two days off, as a reward after one of their best wins this term. How times have changed, less than a fortnight since.

Nine days have passed since that morale-boosting result: they’ve been blasted 4-1 away against struggling Leicester and now Conte’s return to the San Siro was anything but satisfying.

Conte, for more context, had only lost one of his 14 previous H2H meetings (W10, D3, L1) against Milan sides dating back to his first one in 2009. This team were languishing on all fronts across multiple competitions, ending a seven-match winless streak at Torino’s expense late on Friday.

Fraser Forster, stepping into the breach after Hugo Lloris’ knee injury, couldn’t do much more.

He made a double save in vain after Theo Hernandez outmuscled Cristian Romero in an aerial duel, before both he and matchwinner Diaz were denied by the 34-year-old’s reaction stops.

Tottenham have been porous defensively all season and were again guilty of ball-watching, as Diaz reacted quickest to flick home the rebound – Milan gratefully snatching an early lead.

That proved their last meaningful attack of a first-half threatening plenty, but delivering little.

Eric Dier headed goalwards with two half-chances: one comfortably caught by Milan’s no. 2 Ciprian Tatarusanu, the second well wide. Emerson forced the Romanian into another stop from distance after Saelemaekers dangerously dithered with possession in his own half.

You could sense Tottenham were growing in confidence, but failed to make the most of their spell in the ascendancy.

Saelemaekers atoned for his earlier error with a big sliding intervention from an Emerson cross as Heung-Min Son lurked behind him, while a chaotic moment unfolded just before half-time.

Skipp teed up Son with a defence-splitting pass, he forced Tatarusanu into a low save before Kane followed up with a deft chip onto the crossbar – only to see the linesman correctly flag for what was an offside position in the build-up.

Olivier Giroud didn’t get many touches, but was inches away from latching onto Hernandez’s searching punt upfield moments later, another warning sign of how quickly Milan could sting.

In the second-half, Tatarasanu worried many after enduring an injury scare after colliding with Clement Lenglet at his near post. Milan were clinging onto their slender advantage, with Simon Kjaer and Malick Thiaw making important interventions as Tottenham pressed forward.

Rafael Leao wasn’t exactly managing to relieve much pressure in the attacking third, while Giroud was dropping ever deeper to be of service.

By contrast, Thiaw kept Dejan Kulusevski quiet and Richarlison replaced the Swede shortly after Dier was booked for dissent, a yellow card meaning he’ll miss the return leg through suspension.

Olivier Giroud of AC Milan consoles his teammate Charles De Ketelaere of AC Milan during the UEFA Champions League round of 16 leg one match between...

It could’ve gone from bad to worse for the visitors: Charles de Ketelaere almost scored with his first touch off the bench. The £28m summer signing couldn’t connect cleanly at close-range after Giroud’s headed flick-on into his path, with Ivan Perisic scampering the ball clear for a corner.

Thiaw could’ve doubled their lead but headed narrowly wide moments later from a Leao cross, while Kjaer held firm in stoppage-time to thwart Kane baring down on goal as Tottenham were held goalless for the third time already in 2023 – a worrying statistic given their creative depth.

What’s next?

Antonio Conte Head coach of Tottenham and Cristian Stellini Assistant coach of Tottenham look in opposite directions as they sit on the bench prior...
Conte and Stellini (front) on the bench before KO, as Richarlison and Lucas Moura (behind) watch on

Tottenham have four games including three Premier League fixtures, before they host Milan next month – given their form, anything can happen and wouldn’t be particularly surprising.

West Ham and Chelsea on consecutive Sundays in televised coverage, before an away trip to Championship side Sheffield United in the fifth round of this season’s FA Cup three days later.

Julen Lopetegui’s Wolves await shortly afterwards, before perhaps the biggest game of their campaign at home to Stefano Pioli’s men in the second leg.

As for Milan, they’re away at Monza on Saturday before a compelling clash against fellow top-four hopefuls Atalanta next Sunday.

They’ll travel to face a struggling Fiorentina side four days before another away trip, this time 750-odd miles with renewed hope after this gritty-not-pretty showing they can complete the job and make the Champions League quarter-finals for the first time since 2011-12.

Picture source: Getty Images


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