There were boos from Tottenham’s half-time support and sighs when Cristian Romero was sent off for a wild second slot. There was more teasing when Antonio Conte sacrificed Dejan Kulusevki and his fleeting banter with a 4-2-4 system. But, overall, there was only frustration.
Spurs were still in that second leg of the last 16 and yet, at the same time, never really at all, the gap between their telegraphed schemes and Milan’s composure was too pronounced. Conte, who made his long-awaited return to the sideline after his health issues, knew a moment could tip the scales. And yet he never came.
When Pierre-Emile Højbjerg ran from right to left, continued and fired a shot into the top corner, it forced Milan goalkeeper Mike Maignan to tip over. It was the 65th minute and it was unquestionably the first time the crowd had been agitated. It was pretty much the last too, if you don’t count the consternation that followed Romero’s decision to pounce on Theo Hernandez on the right flank.
Harry Kane almost pinched something in stoppage time with a header – of course he did – before Rafael Leão came up the other end to hit the post. But for Spurs, regrets were rare. They were well beaten, their dreams in tatters.
The home crowd wanted a quick start, much like the one Milan made in the first leg when Brahim Diaz scored after seven minutes. But this Conte team isn’t exactly ready to blow down the bloody gates – especially against opponents looking for control and maintaining their form.
It was Milan who tied the game, with Spurs looking stiff and pissed off, as evidenced by the first yellow card from Cristian Romero, who flew into a reckless tackle on Rafael Leão.
He knew that meant he would miss the first leg of the quarter-final if Spurs progressed and the same fate befell Clement Lenglet midway through the first half; an aerial challenge on Olivier Giroud, a lost arm, another expensive booking. This one was tough.
Stefano Pioli recently switched to three backs and there was plenty of flexibility in Milan’s system; Díaz wandering from the right to the No. 10 role, Leão going where the mood took him. Wingers Junior Messias and Theo Hernández pushed high and it was the former who should have opened the scoring.
Milan worked a short free-kick routine after Romero’s yellow card with Sandro Tonali playing the killer pass for Messias.
Ben Davies had bet on the interception and lost. Messias was on the right side to drag unnecessarily at the far post.
It was easy to focus on Conte, his return a prominent subplot. He was last seen on the touchline at San Siro three weeks ago when he looked unwell and was quickly ordered to rest. He had counted down to this, Spurs’ biggest game of the season, the crowded stadium, the incredibly bright colours.
The first half was difficult for him and Spurs support, who struggled to quell their frustration – whether it was Ivan Perisic being robbed as he tried to guide the ball, Davies hurting overpowered or Son Heung-min passing a cross. Still, it was remarkable to hear a few boos at the half-time whistle. They were even louder at the final whistle.
Milan gained comfort on the ball before the interval, with Díaz and Tonali attracting attention, partly because Spurs failed to bring any kind of press. Conte’s team wanted to counter, but apart from an early push from Harry Kane, which led to a shot from Emerson Royal which was blocked, they did nothing. It was too static and predictable.
There had been drama before kick-off, the roads in north London were blocked, leaving the team buses to move slowly. Would they arrive in time? He felt himself touch and go. Spurs would finally come in at 7 p.m., Milan five minutes later. Kick-off was delayed by 10 minutes.
The atmosphere failed to crackle up to and including the interval when former Spurs captain Steve Perryman went a long way in the past as a guest on the pitch. Conte’s side had to come up with something in the second half, anything, because at 0-0 it only took them a moment. Similarly, the crowd would never need much to rally. Just something, anything.
It hasn’t been a good season for Milan, their title defense long in tatters; fifth in Serie A. Chelsea dominated them home and away in the group stage of this competition.
And yet they looked good here, with Díaz playing his own game at times. He traded passes with Messias in the 52nd minute, earned a break and forced Fraser Forster into a smart block.
Conte’s introduction of Pedro Porro injected energy and there was a feeling, perhaps just a hope, that Spurs were preparing for a grandstand finish when Højbjerg extended Maignan. Belatedly there was life, although Milan continued to threaten at the break. Then came Romero’s recklessness. It was never Tottenham’s night.