Tottenham’s whimpering Champions League exit spells the end of the Antonio Conte era

Harry Kane captained a Spurs side that failed to land a punch in their last-16 second leg (Action Images via Reuters)

Arrivederci Antonio? If not the end for Antonio Conte, this surely seems the beginning of the end. Conte’s comeback to the dugout lasted a solitary game in the Champions League as Tottenham exited the competition with an evening that illustrated the flaws and failings of his gameplan. They paid a price for a performance of utter pointlessness in the first hour. They were depleted by Cristian Romero’s idiocy and defeated by their own dullness.

Tottenham’s motto is “to dare is to do” but Conte has the least daring of teams. They failed to score, rarely tried to and missed the chance to follow in the footsteps of Mauricio Pochettino’s altogether bolder side, who reached the 2019 final. His Champions League record remains resolutely mediocre and his next game in this competition will surely be with another club.

A former Inter and Juventus manager went out to AC Milan and if a storied club could celebrate that, more pertinently for the seven-time winners, their wilderness years may be ending. For the first time since 2012, they are quarter-finalists. A 0-0 draw was a triumph for them. If Stefano Pioli’s team scarcely look one of the great Rossoneri sides, they showed resilience and organisation, a brightness on the break and a composure that Romero lacked.

The red-carded World Cup winner was not alone in incurring referee Clement Turpin’s displeasure. Conte marked his return to the technical area with a caution for dissent. By the end, however, more were displaying their displeasure with him. There were boos when he replaced Dejan Kulusevski with Davinson Sanchez, albeit to compensate for Romero’s departure. They reflected his image as a safety-first manager.

As is often the case with Tottenham, it was a moot point if it was a game of patience or impotence, a question if it was strategy or negativity. The answers felt unflattering for Conte as, for the third consecutive game, Tottenham failed to score. Neither side had a shot on target for 50 minutes but the extended impasse was a scenario that suited AC Milan better. Spurs played as though unaware they kicked off with a one-goal deficit. There was a lack of urgency which was both unsurprising and damning. They played with a passiveness that was both strange and typical. Conte’s Spurs are rarely swift starters and for the sixth consecutive game they did not score a first-half goal. Nor, really, did they threaten one.

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They belatedly stirred, partly when Conte had to abandon his favoured formation, only to be undermined when Romero exited in ignominy. The Argentinian’s recklessness and rashness again went into the realms of stupidity. He got an early booking for the least subtle of fouls on Rafael Leao. He then flew into Theo Hernandez. A second red card of 2023 was the inevitable outcome.

Cristian Romero’s ugly tackle saw him get sent off as Spurs were reduced to ten men (AFP via Getty Images)

Spurs could still have taken the tie to extra time. Harry Kane’s injury-time header was clawed away wonderfully by Mike Maignan. Yet if the Frenchman may be the best goalkeeper in Serie A, he rarely had to be: he was not tested at all until Pierre-Emile Hojbjerg’s rising shot after 64 minutes. Milan recently conceded five goals to Sassuolo. There was never a danger of a repeat from Spurs.

If nothing else, Conte was true to himself. A back three is set in stone, Son Heung-Min was preferred to Richarlison and Pioli could have guessed the Tottenham team. The Korean, once again, was ineffectual, Kulusevski too slow whenever he was in a race and, with 20 minutes remaining and a stalemate beckoning, Conte was forced to change, summoning the Brazilian, going to 4-2-4, at least for 10 minutes.

Yet Milan long looked comfortable. They had points when they penned Spurs in with a high press. Catenaccio it was not. They threatened with cunning planning. Junior Messias arrowed a shot just wide after a clever free-kick routine.

They had the elusiveness, the deft touch and sharp turns of their San Siro matchwinner Brahim Diaz. He conjured the game’s belated first attempt on target, exchanging passes with Messias, wriggling through and being denied by Fraser Forster. His quick footwork led to Milan’s next, when Forster thwarted Olivier Giroud.

Antonio Conte’s Tottenham tenure appears to be ending (Getty Images)

And Milan had a threat on the counter-attack and the pace of Leao and Hernandez offered them outlets on either flank Spurs resorted to the illegal to halt the Portuguese. When Giroud went off, Pioli brought on Divock Origi, a super-sub perhaps designed to remind Tottenham of better days.

The Belgian had finished them off in the 2019 final, during his Liverpool tenure. Seconds after Maignan denied Kane, he had the chance for a repeat, breaking clear, hitting the post. It spared Tottenham a third defeat in eight days. But after Sheffield United and Wolves, their season has been sent into a tailspin and with it Conte’s reign.