How will Tottenham fare following their late transfer window business?

Joao Moutinho. Leandro Damiao. Willian. Morgan Schneiderlin. Names that Spurs fans know all too well for the wrong reasons.

Tottenham’s transfer strategy has never been a perfect one, even if no one else’s is. Trying to replace what’s left for less than or equal to what was raked in is difficult when you’re a consistent top six outfit. If you stand still, you move backwards.

The four names listed are the ones that got away. Some hit snags with monetary issues, some clubs didn’t want to sell, and some were whisked away at the eleventh hour to Stamford Bridge.

But I digress.

For the seasons which followed without the ones that got away, fans were left wondering ‘what if’. How could those players have slotted in? How many more points could they have won?

Every club has these kinds of issues though, Tottenham aren’t alone. Last season, however, Spurs appeared to have got one of those deals over the line.

Within 24 hours of first being reported by any media, Tottenham had secured the £22m signing of Heung-Min Son from Bayer Leverkusen. One of the quickest dealings in the recent memory of the White Hart Lane faithful; when Daniel Levy is chairman, nothing ever seems easy.

Both at the time and in hindsight, Son’s transfer seemed like a rumour that wouldn’t really come to fruition. Another name confined to the dust and cobwebs of transfer rumours.

Although Son’s debut campaign in England wasn’t the most memorable one, he did provide some memorable and crucial moments in Spurs’ title-challenging season.

Late winners versus Crystal Palace and Watford quickly put him in the good books of his new fans, and even after a few months of mediocrity, returned with smart strikes against Chelsea and Southampton.

The latter two goals may not have counted for much, but his impact in the first-half of the season gained Spurs four more points, crucial in their quest for a first league title in 55 years.

Fast forward to the end of this window, and Tottenham may have pulled off another such deal.

Moussa Sissoko is hardly the most talented player on Earth, and had garnered a reputation at Newcastle United for being lethargic and largely a moments player. A £30m late switch to north London from afar made little to no sense.

But there is method in the madness.

Spurs’ latest addition, Sissoko, scored just one goal in 37 league games for Newcastle last term – Photo: Mark Leech / Offside.

Following Spurs’ disappointing 1-1 draw with Liverpool, Mauricio Pochettino bemoaned a lack of directness and aggression in his team’s attack. He claimed he wanted a player like the Reds’ Sadio Mane to bolster the squad.

Sissoko at this moment doesn’t fit that mould, but the Argentine clearly thinks he can work his magic with the French international.

It was reported that chairman Levy has a rule when it comes to transfers – never spend more than £20m on a player over the age of 25. At 27, Sissoko would have to be a special case in order for the chairman to sanction the deal.

So what made Levy cave in?

Rumours of a loan deal for Isco circulated in the last few days of the transfer window, but nothing came of it. With only Vincent Janssen and Victor Wanyama the only players signed heading into deadline day, there was clearly some unrest at Hotspur Way.

Surely Tottenham wouldn’t be heading into a Champions League campaign with such little squad depth?

Deals for Marseille winger Georges-Kévin Nkoudou and Espanyol goalkeeper Pau Lopez were finally tied up with hours to spare, but Spurs still lacked serious cover in midfield.

At the time of the Nkoudou and Lopez confirmations, Sissoko appeared to be heading to Everton, with a medical prepared for him on Merseyside. A few missed phone calls later though, he was pictured in Lilywhite.

A deal so late for such a high fee clearly indicates Pochettino’s belief in himself to bring the best out of him. Why wouldn’t he? A year ago, Mousa Dembele appeared to be heading to Sunderland after a poor start to the season, but ended the year as by far and away one of the Premier League’s best midfielders.

If Pochettino can get the same out of Sissoko, then maybe Tottenham’s transfer window will have been a great one after all.