For Antonio Conte, it had been easy to wonder which Tottenham would turn up for the biggest game of the season so far. The team that outplayed and beat Manchester City on the Sunday before last? Or the one which collapsed at Leicester on Saturday?
Conte has craved consistency, a little stability and it was not for nothing on Monday night that he likened life at the club to a rollercoaster. This was the latest ride. The manager, who continues to recover from the after-effects of his gallbladder removal two weeks ago, felt his insides churn when Brahim Díaz scored for Milan with the tie’s first action.
The one-time Manchester City forward scored at the second attempt after Fraser Forster – starting in place of the injured Hugo Lloris – had repelled his initial effort in quite breathtaking fashion.
At that point, with the San Siro rocking, Spurs could have caved. This Champions League last-16 tie might have got away from them. That they shook their heads clear to produce a performance of calm and control was encouraging. For long spells, it did not feel as if they had too much to fear from a Milan team that has struggled on the domestic front since the turn of the year.
Yet it almost lurched away from them towards the end when Stefano Pioli’s team passed up two huge chances. Rafael Leão, Milan’s shimmering talent on the left wing, was at the heart of them, slinging over a pair of crosses. Olivier Giroud nodded down the first for the substitute Charles De Ketelaere who fluffed his lines badly. On the second, Malick Thiaw muscled in and he had to score only to head wide.
The downside for Spurs lay in how they laboured to create much of clearcut note. Eric Dier, who was harshly booked and will be suspended for the second leg, had a free header late on from an Ivan Perisic corner but he got his calculations wrong. There were a few other flickers from Spurs, mainly from set pieces, but Milan kept them largely at arm’s length.
Spurs had created a few previous legends at one of the great cathedrals of European football – the Gareth Bale hat-trick against Internazionale (albeit in defeat); the Peter Crouch winner against Milan in a tie more famous for Gennaro Gattuso versus Joe “Jaws” Jordan; the Emmanuel Adebayor goal that edged a Europa League thriller.
Their mission to create something more up to date was hampered by a selection crisis – a clutch of serious injuries plus Pierre-Emile Højbjerg’s suspension – and set back by the early concession.
Théo Hernandez got the better of Cristian Romero in an aerial duel and just kept on running up the left, unloading a shot before Dier could get across which forced Forster into a smart parry. In came Díaz, who shot and it looked as if Forster could be the hero when he threw out his left hand to save. Not so. The ball looped up and Díaz flung himself into the diving header to score. Díaz’s run and reflexes were simply too sharp.
The sold-out stadium was a picture; the atmosphere pulsating. “Non ti ho tradito,” read one of the banners before kick-off. “I have never cheated on you.” There were various other messages proclaiming the collective love for the Rossoneri. It was Valentine’s Day, Milan-style.
Milan’s threat came up the left. Hernandez was in the mood to rampage while Leão showed his love of the big occasion, comfortable on the outside or slicing inside. His only thought was to be direct and hurt Spurs.
Conte’s team stabilised after the Díaz goal, coming to enjoy possession, working combinations in enemy territory. They were the better team for the remainder of the first half. Harry Kane dropped off to link the play – when he was not being fouled by Simon Kjær – while there were a couple of occasions when Spurs won the ball high up to threaten.
There was always going to be a focus on the inexperienced midfield duo of Oliver Skipp and Pape Matar Sarr. They had started together only once before – in the FA Cup against League One Portsmouth. Both emerged with honours, particularly Skipp; they made big tackles and showed real polish in possession.
It was a homecoming for Conte, back at the stadium where he won the 2020-21 Serie A title with Internazionale. The boos when his name was read out were loud and predictable; ditto those for the former Inter player, Perisic, and Dejan Kulusevski, previously of Juventus.
Romero played on the edge, as usual, the travelling fans watching through their fingers when he was one-on-one, including the moment when he jumped into a challenge on Sandro Tonali that he was never going to win. It brought a booking on 48 minutes.
More costly and controversial was Dier’s yellow card. Giroud was going nowhere in the middle of the pitch, heading away from goal when Dier pulled him. It was a kick in the guts for Spurs, who have had a few of them in recent times. What was clear as Milan celebrated in front of their fanatics was that the return in London is beautifully poised.
