Tottenham face make-or-break three months as Harry Kane reaches decision-time on his future

This is bad, isn’t it? Tottenham’s latest ignominious FA Cup failure was not only more shameful than the rest because it came against a Championship side who had made eight changes – that part didn’t even feel unfamiliar. They went out to Middlesbrough on the same date last March. Happy anniversary.

The stings do get sharper with every passing year though – 15 since the last trophy and 32 since the last final in the cup. Even if Chas & Dave were still making records, they wouldn’t have much to sing about. Spurs rarely are on their way to Wembley anymore, and no one at Bramall Lane would have described them as Hot Shot Tottenham.

But what made this particular low even more agonising was the way the cup had neatly opened up for Spurs, who it turns out would have been a home tie against Blackburn away from the semi-finals. There – depending on the draw – they might have ended up with Brighton or Grimsby Town. Then again, even the Mariners knocked them out of the League Cup in 2005.

There is one Chas & Dave cup final song which could probably still make its way into the repertoire, the 1982 classic Tottenham Tottenham (We’re going to do it like we did last year) – “it” being a humiliating exit to a lower-league side on a freezing cold night in Yorkshire. Conte’s No 2, Cristian Stellini, said his players remembered being “disappointed” by the Middlesbrough performance a year ago, but it felt like no lessons were learned.

Without Cristian Romero or Harry Kane, who had been ill with “a throat problem” and was brought on after the hour mark, it wasn’t entirely clear whether Spurs thought they could waltz through one of the domestic cups without really trying, or if they knew they would be knocked out and didn’t care.

Where exactly does this leave them? For one, with little time to prepare for Saturday’s trip to Wolves and with another all-encompassing sense of doom that they had just done so well to shake off. Wins over Manchester City, West Ham and Chelsea had things looking a lot rosier – Antonio Conte was nominated for manager of the month without even being there as he recovers from surgery.

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Yet the uncertainty surrounding Conte makes this moment a little more troubling. There are three months of the season left and he is still yet to indicate, at least publicly, whether he is staying or going when his contract ends in June. To some, that tells you everything you need to know, but it isn’t conducive to long-term planning. Conte not winning a trophy is not viewed as a major failure – he isn’t guilty of anything you couldn’t also say about his predecessors, yet he hasn’t done any more than them either.

Kane, too, cannot be thrilled with the situation. This was perhaps his last serious opportunity to win a trophy at Tottenham. He already has the individual records. The club’s greatest ever goalscorer and the England captain, who has played in four major finals for club and country but not yet won one, needs more. By June he will be available at a cut-price fee with just a year left on his contract. It feels as if a decision will have to be made either way this summer.

To Wolves then, where another step towards the top four is the aim. Champions League football is considerably more lucrative, and arguably does more for Spurs’ status than winning either of the domestic cups, which by degrees the club has valued less and less. Otherwise, they would not have sacked Jose Mourinho six days before a final.

The trouble is, since 2015-16 they have finished in the top four more often than not. Even after a brief foray into the Conference League, a place at the top table is, at best, greeted with polite applause. At worst, it can easily be taken for granted.

Kane will return for the trip to Molineux, where Richarlison will once again have to adjust to a system that does not suit him. The Brazilian’s role is ever divisive – after Wednesday’s defeat, one pundit said he had “no standout attributes”; another thought Manchester United should be signing him.

In-form Emerson Royal is likely to come back in for Pedro Porro, while Oliver Skipp and Dejan Kulusevski are set to start rather than come off the bench. Romero will replace Davinson Sanchez but apart from that, this will largely be the same XI that Stellini insisted should have been good enough to beat Sheffield United.

In a full circle, it comes back again to recruitment. Spurs have spent tens of millions on players they have not even used – see Djed Spence and Destiny Udogie, who is out on loan, and on Richarlison who they are not getting the best out of. If they were to lose Kane and Conte this summer, they would not just be doing it like they did last year. It could get considerably worse.

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