Something doesn’t feel right at Tottenham and it hasn’t for a while. Jose Mourinho, after so much promise, has struggled to convince fans he is the manager he once was and if Tottenham don’t get into the Champions League for next season – what will the coming years look like? Spurs are at a crossroads and unless they can plan accordingly, they run the risk of returning to the mind-numbing era of the late ‘90s.

Take, for example, December 1997. Tottenham have lost 6-1 to Chelsea at home and in seven days will lose again to Coventry. Four nil, to be precise. Darren Huckerby will get two goals. A month before Gerry Francis resigns as the Spurs manager as the club becomes sucked into a relegation fight. Chairman Alan Sugar appoints Christian Gross who arrives at his first press conference flashing his London tube ticket with the words: “I want this to become my ticket to the dreams”. David Brent eat your heart out.

Gross responds to the humiliating loss to rivals Chelsea by re-signing Jurgen Klinsmann, a fan favourite following the 1994-95 season where he won the 1995 Football Writers’ Association footballer of the Year after scoring 29 goals. Within a few months, Tottenham are knocked out of the FA Cup by Barnsley and Klinsmann will declare “I have totally different views about the way we should play” in relation to Gross’ tactics.

The club will eventually confirm their status in the Premier League after beating Wimbledon with one fixture to spare. Klinsmann scores four times in a 6-2 win before retiring from football. The German striker remains idolised by Tottenham fans to this day.

Gross will leave Spurs in September 1998 but before that he’ll sign unknown Paolo Tramezzani from Piacenza in the summer. Meanwhile, Arsenal sign Freddie Ljungberg and Chelsea secure the services of Marcel Desailly from AC Milan. Spurs were not the London force they are today.

Tottenham might’ve been in the Champions League final eight months ago, the peak of European club football, but there a lot of Spurs fans who can remember a demeaning time of mid-table scarcity during the ‘90s as well as humiliating defeats; most notably the eight goals conceded against FC Koln during the Intertoto Cup in 1995.

Fast forward to the club’s recent history and fans laugh at the mediocracy of the “Spursy” years. It’s been 10 years since they’ve finished outside the top six – which was the “big four” prior to Man City’s money and Tottenham’s pure football disrupted that party. Since 2015 the club have been an ever-present in the Champions League. Heck, Spurs are now the richest club in London and the eighth in the whole world. Add a new stadium to that list and things are looking very positive.

The run-up to the Champions League final, with all its drama, masked other issues. Spurs lost 14 league games in 2019 – more than Crystal Palace and Wolves – compared to the 14 for the previous two years combined. Mauricio Pochettino has been fired as Tottenham manager with Mourinho appointed as his replacement.

After winning his first three games in charge Spurs have stumbled in the league with the biggest concern being the number of goals conceded. Mourinho has prided himself on clean sheets at the other clubs he’s managed and the only positive to be taken after a recent bore draw against Watford was the strength of the defence. The lack of chances created will now be another issue for fans.

Mourinho has said he doesn’t want Spurs to lose their attacking qualities. In his first few games this strategy looked to be paying off as Dele Alli, Heung-min Son, Lucas Moura and Harry Kane all scored and created goals. The Spurs manager asked his team to play with their “instincts” in attack, but instincts should be no substitution for coaching and providing players with new ideas.

Jurgen Klopp, in comparison, has clearly worked with his side on attacking phases of play and creating chances from overlapping fullbacks or by third-man runs from midfield players which provides their attackers with the space to score. Tottenham’s forward movements are now easy for any analysis department to predict and create strategies to nullify attacks.

The biggest concern to any Spurs fan, however, should be Kane. From one perspective his current hamstring issue might look like yet another injury that prevents him from completing a full season – like his ankle injuries over the past two years. Tottenham’s reliance on his world-class talent and their inability to sign another striker to compete with him has caused the striker to look fatigued and lack mobility.

Even if he does make a full recovery from his injury issues and gets back to his goal-scoring best, he might decide to leave the club if his ambitions are not met. Kane would’ve been disappointed to not have won the Champions League final but would be expecting to compete for trophies and be challenging for the league.

The striker has said “keep progressing, keep getting better…as long as the club keep doing that then, yeah, I’m happy here”. Tottenham are no longer progressing and any club in the world would take Kane which could trigger a potential demise of Spurs similar to the Christian Gross and George Graham years.

If Kane did leave it would feel like a Klinsmann de-ja-vu; a top striker wants to achieve their dreams with a club they love yet still feel they’ve got to leave in order fulfil ambitions. Aston Villa, Blackburn Rover and Sunderland have shown us if a club is not planning to go forward it’ll go backwards. Very fast.

The relegation-threatened days of the 1997/98 season may come flashing back but this time – given how the modern game works – Kane won’t be coming back to save the day like Klinsmann once did.

Mourinho would’ve been long gone by this time. Tottenham are a team which historically struggles with transition when changing long-standing managers. Gerry Francis, Martin Jol, Harry Redknapp and Pochettino’s tenures were sandwiched with the failures of David Pleat, Jacques Santini, Juande Ramos, Andre Villas-Boas and Tim Sherwood. Mourinho is looking like he could be added to this transitionary list.

The late ‘90s were an odd, and often embarrassing, time for Spurs and their fans but with strategic visioning, as well as a bit of luck, they have been able to be relatively successful over the past decade. The time for luck has gone – every club receives a stupid amount of money for just being in the Premier League. If Daniel Levy is not prepared to be bold and take risks – there are 19 other clubs ready to take your place.

What felt like a golden ticket for Tottenham eight months ago – to reference Gross – with the new stadium and a Champions League final is fast becoming a distant dream for Spurs. Going back to the performances of the ‘90s would be the ultimate nightmare.