Tottenham were beaten by themselves as much as they were undone by Milan in the Champions League

Milan 1-0 Tottenham (Diaz 7’)

It wasn’t supposed to be this hard work. Tottenham may well still qualify for the Champions League quarter-finals, for they were beaten by themselves more than outplayed by a proficient opponent. But the same auto-response on repeat, every time you watch this team: why can a team that commits so little to their attack look so clumsy in their own half? We are 16 months into this arrangement and, if you do have an answer, send your answers to White Hart Lane and copy every supporter in.

In truth, this first leg rarely had the feel of a Champions League knockout match. The San Siro more than did its bit – however they eventually replace this stadium, they will never replicate the manner in which the shrieks and roar reverberates and the seats shake beneath your feet. But on its bobbly, frankly unfit-for-purpose brown-green pitch, the football had the whiff of Europa League. Both teams were grasping for form, confidence and, at times, mere competence. Passes were misplaced, clearances shanked, crosses overhit more often than not. Twice players from the same team bumped into each other for no obvious reason. You really want it to be better than this.

The inexperience of Tottenham’s midfield pair was frankly extraordinary. Like pretty much everything else within Conte’s Spurs, misfortune and mistakes had combined to leave them without Rodrigo Bentancur, Pierre-Emile Hojbjerg and Yves Bissouma. Reach far enough into the back of the kitchen cupboard, behind that half jar of turmeric and the Italian herbs, and you find Pape Matar Sarr and Oliver Skipp. This is harsh; both are young and may well become exceptional midfield holders, strollers or patrollers. But they also combined for 58 career minutes in the Champions League before Tuesday.

That would have been a permissible excuse, if Sarr and Skipp had been caught like two spring leverets caught in the headlights or unnerved by an atmosphere that shook the stadium and has broken the resolve of more experienced players. But they were two of Tottenham’s best players. Sarr looked composed and has a gorgeous way of shifting his weight from one foot to the other to shimmy past an opponent. Skipp was the snapping pressor and tidy passer and also excelled. He has been a Spurs season-ticket holder for most of his life and has made a dream come true.

Instead, it was those who should know better that did no better. Cristian Romero, who started his Spurs career wonderfully, has become reckless since the World Cup. He has developed a habit of steaming out to meet an opponent whether he has a shot at winning the ball or not; Theo Hernandez delighted in leaving him sprinting at thin air. Milan’s best moments, and their goal, were delivered by Hernandez’s left boot. Romero at least got his way eventually, booked for a nasty, reckless tackle on Sandro Tonali.

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The wing-backs still aren’t working either. These are supposed to be Conte’s magic trick, the tactical philosophy set in stone that his peers had never quite managed to solve. It doesn’t help much that Ivan Perisic has been desperately below the standards of his previous seasons. For Tottenham to work on the counter with Perisic involved on the left, he needs to stop turning back onto his right foot and playing backward passes. Also, quick tip: the goalkeeper can use his hands so don’t aim all your set pieces towards him.

There is also, dare we say it, a brainlessness to some of Tottenham’s play. Exhibit A: Milan were happy to play for time and a high ball looped into Ciprian Tatarusanu’s gloves. At which point Clement Lenglet barged into him and provoked a predictable two minutes of superfluous treatment. Lenglet was ragged with and without the ball all evening, epitomised by a shot from distance with eight minutes to go that went 25 yards over the bar and a cross that missed its targets by probably double the distance.

Milanese football, which was reawakened with such vigour and clarity last season, is once again creaking like the beams of its grand sporting theatre. Stefano Pioli, the Rossoneri’s glorious protagonist just nine months ago, is quickly falling back towards the upturned sword. “Pioli has lost his Milan,” read La Gazzetta dello Sport‘s headline..

That is the greatest damnation of Tottenham under Conte over the last four months. Not only can their opponents sniff victory when they too are below their highest ebb, but Spurs are the perfect tonic. Need a shot in the arm? Call Conte the anaesthetist. Want to feel better with notable results in just 90 minutes? Call Dr Tottenham. Back in the city where one half of its population recently called him king, Conte’s side have become a rabble of paupers. There are precious few exceptions; they must be wondering if it’s all worth the effort.

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