Seven years have passed, countless players and managers have come and gone, yet that night in Madrid still sticks in the craw for Tottenham Hotspur.

All the build-up, all the excitement ahead of a first Champions League final was burst inside a minute as Premier League rivals Liverpool were awarded a controversial spot-kick, the Reds going on to coast to a 2-0 win following Divock Origi's late clincher.

The decision to penalise Moussa Sissoko for 'handball' still appears distinctly harsh, although perhaps this was always set to be a step too far for Mauricio Pochettino's side, not least considering the starting midfield that day had been the Frenchman and Harry Winks.

Sissoko, a powerhouse figure at his best, certainly had his merits, but the north Londoners appeared to have favoured his physicality over technical quality when signing off on the deal. No lessons learned there, then.

Why Spurs signed Moussa Sissoko in 2016

Spurs left it late to do business this summer, and it was no different a decade ago, having snapped up the signing of Sissoko late on deadline day.

The then-Newcastle United man had looked to be on his way to Everton before Spurs leapt in with a bid of their own, snapping up the rampaging midfielder for what was a club record fee at the time of £30m.

27 at the time, Sissoko was fresh off the back of a strong Euro 2016 campaign with France, albeit having also been part of a Magpies side that had slipped to relegation that season.

Even so, Daniel Levy and co were willing to take the punt, with journalist Jack Pitt-Brooke, then writing for the Independent, highlighting how Pochettino had demanded more pace and athleticism to freshen up his midfield ranks.

Spurs, even with Sissoko having struggled for 'consistency' in Pitt-Brooke's view at St James' Park, saw the merits of signing a player who could operate on the flanks and in a central role, someone who could instantly hit the ground running due to his prior Premier League experience.

It's fair to say it didn't exactly pan out that way for the 6 foot 2 enigma.

Why Sissoko wasn't a successful signing for Spurs

Sissoko's starting berth in the 2019 showpiece did illustrate the resurgence he'd had after a difficult start to life at White Hart Lane, yet even so, this felt like a deal that was never truly going to work out for the north London side.

Sissoko, considering his age, didn't exactly feel like a Levy-style signing, nor did he appear to fit the Pochettino mould, the Argentine overseeing the rise of so many young talents at Tottenham, be it Harry Kane, Dele Alli or Heung-min Son.

The woes of others, and the shift in a central midfield berth, did spark an eventual improvement for Sissoko, even to the point at which he secured almost cult status among the Spurs faithful.

That 'cult' tag can often be almost a backhanded compliment at times, a player setting the bar so low initially that their subsequent rise in form is ultimately a little overblown.

Indeed, the key issue for Sissoko was simply his woes in possession, recording just an 82% pass accuracy rate in his debut season, while never providing more than 0.9 key passes per game in a Premier League campaign for the club.

Five goals and 16 assists in 202 games also makes for grim reading for an attack-minded, box-to-box figure, with a man among Spurs' current crop looking on course to suffer a similar fate in a Tottenham shirt.

Spurs move for the modern-day Sissoko has already backfired

The key talking point for Roberto De Zerbi's side this summer was the midfield unit, with ENIC splashing out £185m to seal the signings of Mateus Fernandes and Sandro Tonali.

Three games into the new league season, the Italian is still yet to settle on a first-choice combination, however, with the relatively long-serving Rodrigo Bentancur still the star attraction in that department.

That doesn't reflect well on either Tonali or Fernandes, nor does it on those signed in the recent past, be it Archie Gray or Lucas Bergvall, the pair joining in 2024.

Perhaps the biggest point of concern lies with a man who only joined the club in January, Conor Gallagher, with the £35m signing already like Sissoko mark two.

Like the polarising Frenchman, Gallagher looked initially like a smart pick-up due to his prior Premier League experience with the likes of Chelsea, Crystal Palace and West Bromwich Albion, having not exactly been a disaster either at Atletico Madrid.

At 26 too, like Sissoko the Englishman felt like someone who could immediately come in and make an impact, the midfielder such a bundle of energy and athleticism.

His full-blooded, committed approach will win plaudits, as it did for Sissoko, but again, like the former Spurs man, there remains an issue over both his best role and his suitability for the manager in the dugout.

It's hard to know where best to place him, with Gallagher arguably not creative to operate as a number ten, not good enough on the ball to operate as a number six or number eight, yet also not a strong enough dribbler to thrive on his flanks.

Yes, he can have his moments, like his thumping effort against Aston Villa last season, yet the £35m man's record already looks a little underwhelming, contributing just one goal and one assist in his first 20 games for the club.

Against Nottingham Forest last time out, it felt like a typical Gallagher - or even a typical Sissoko - performance, full of endeavour and work rate, yet lacking in anything of substance in possession.

He won nine of his ten ground duels and did actually enjoy a 94% pass accuracy rate, although the all-action midfielder failed to register a single key pass or attempt a single dribble.

Maybe his workmanlike approach will be enough to endear him to both his manager and Tottenham supporters in the long run, but is there really enough to his game for Gallagher to genuinely prove a success at N17?

If handing the 22-cap England international a rating out of ten right now, a three might well be a fair assessment considering his lack of end product and inability to hold down a regular starting berth, with questions still needing to be asked as to why ENIC signed off on this deal in the first place.