Despite Spurs’ wretched season there have been times this year when they might have turned a corner. A first win in their new stadium against Chelsea, Harry Kane breaking Jimmy Greaves’ scoring record on the day they beat Manchester City, even their mildly encouraging performance in the first leg of this Champions League tie against AC Milan, despite a 1-0 defeat.
Here for the second leg the corner never even came into view. Instead, Spurs were on a steady and straight road to nowhere.
Next season it seems inevitable there will be no Antonio Conte and if these listless performances continue there will be no Champions League. As this dog of a game wore on it became hard to imagine what might persuade one of the world’s best strikers to stay with his club.
Few in football wear despondency like Harry Kane. It is partly why so many non-Spurs fans say so frequently, so unusually, that they feel sorry for him. The inference is that Kane might deserve a better shake in the football lottery, as if the team he plays for is some unfortunate accident of fate.
When he and his team-mates are toiling fruitlessly, as they have done so many times under Conte, his face is a doleful picture of disappointment. He is an innocent bearded child with hope in his heart, being forced to watch football snuff videos of free kicks being endlessly blasted into walls. Surely he cannot take much more of this?
He is not without blame. Not for the first time in similar circumstances Spurs needed a big night from their captain and got anonymity: one shot on target, zero meaningful dribbles or key passes. Milan defender Simon Kjaer nullified him in the first leg, and was promisingly only on the bench on Wednesday night. No matter, the Italians’ back three found it easy to limit the England captain’s involvement to those vaguely desperate deep drops, searching in vain for the raking pass which would open up an obstinate defence.
That tactic only works when Son Heung-min is on form rather than a shambling irrelevance. Spurs’ front three seemed to be operating not just on different bandwidths but with incompatible methods of transmission, Kane’s DAB speaking a different language to Dejan Kulusevski’s FM while Son could only offer the quaint nostalgia of medium wave.
The problems were not just up front for Kane and Spurs, with a claggy midfield duo of Oliver Skipp and Pierre-Emile Hojbjerg which on this form would struggle to light up the Europa Conference League. Despite it all the Harry of the Hotspurs moment presented itself in the 94th minute, Kane heading a Son free-kick powerfully into the ground. The stadium began its celebratory roar as Kane rose in slow motion, towering above marker Rade Krunic for what felt like the first time all night. It was well saved by Mike Maignan.
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On what should have been a night of fervour, Spurs’ supporters were largely silent. Towards the end of the first half the big screen picked out three fans wearing identically nonplussed expressions. As two minutes of injury time was announced they looked as if they were in an airport terminal awaiting repatriation after a natural disaster, and had just found out they would be flying home with Ryanair.
Everything hurts for Tottenham now, and it is so much worse when they look around at their neighbours. Arsenal topping the league is bad enough, but Chelsea’s kitchen sink tactics against Borussia Dortmund provided a template of how to approach this game. Where was the cavalry, the great siege, the wave upon wave? A reckless red card for Cristian Romero was all they could manage.
So now several months of marking time, counting down and potentially preparing for two major goodbyes. While there is sympathy for his annus horribilis, few tears will be shed for Antonio Conte and his frequently brutal football.
Bidding Kane farewell would be different, a tragic parting between Spurs and one of their own. But the sullen 60,000 here could be in no doubt. They might have seen his last game for their team in this competition.