It’s the 22nd of October 2017, Tottenham Hotspur had just embarrassed Liverpool in a 4-1 hammering at Wembley Stadium.

Fast-forward four and a half years, Liverpool have a Club World Cup, Super Cup, Premier League and UEFA Champions League all stored up in their trophy cabinet, whilst Tottenham have experienced more managers than the number of trophies Liverpool have won.

Luiz Diaz transferred to Liverpool on the penultimate day of the January transfer window after hijacking Tottenham’s move for the winger (The Sun).

The Colombian reportedly opted for the Merseyside club due to their long-term interest and Tottenham hesitating in negotiations (Bluradio via Liverpool Echo).

Diaz intensified the long list of Tottenham failed transfers, including a whole host of big names over the past five years. It always seems like Tottenham fail at the last hurdle or back out of that special move that can take the squad to the next level.

Diaz had scored 14 times and assisted 4 times in just 18 starts for FC Porto (FotMob) to attract Tottenham and Liverpool’s interest. Those eye-watering numbers would have seen Spurs pushing to engineer a phenomenal attack of Son, Kane, and Diaz.

However, it was Liverpool who were the club to close a deal by swooping in after Tottenham’s leaked bid (Telegraph).

This efficient approach to the market and ability to attract players is a clear measure of success and progress for Tottenham over the past years.

As mentioned previously, Tottenham beat Liverpool 4-1 in the 2017/18 season, at that point, Liverpool had just signed Egyptian winger Mohammed Salah along with little known Hull City left-back Andrew Robertson.

Klopp’s Liverpool were struggling to match the levels of teams like Tottenham. That changed over the course of the season; however, Liverpool backed Klopp to pull the reds out of their rut, signing Southampton centre-half Virgil van Dijk in the January transfer window for a seemingly extortionate price, although, with hindsight the effect that Van Dijk had on the Liverpool team was priceless.

Both Liverpool and Tottenham fell one short of glory that season as Spurs lost out on the Premier League title to London rivals Chelsea, and former Tottenham winger Gareth Bale fired Real Madrid to European glory at Liverpool’s expense.

The season after, Tottenham didn’t spend a penny in the market, actively imposing a two-window transfer ban on themselves, undoubtedly, to help finances after them being stretched with the construction of a new stadium.

Liverpool, however, took further action towards strengthening their promising side, they spent a total of £164 million on transfer in the summer of 2018. Alisson arrived for a substantial £56 million along with Keita, Fabinho and Shaqiri (TransferMarkt).

The new men in Merseyside helped form a rebuild of the club, clearing out deadwood and bringing in fresh new players had proved a valuable move as Liverpool finished second in the Premier League.

A season on from Tottenham’s thrashing of Liverpool at Wembley the two clubs met at the Metropolitano Stadium for the Champions League final.

Tottenham’s squad had become tired but managed to achieve a 4th place finish in the league and with Lucas Moura’s heroics the club had made the Champions League final with the absence of star striker, Harry Kane.

Kane was in a race against time to reach the final, a situation that possibly may not have occurred had the club spent money in the summer for a backup striker to lighten the load for Kane.

However, Kane had won that race against time and started the final, controversially causing Lucas Moura to be omitted from the starting line-up despite his magic in the previous round.

Tottenham fell short at the last hurdle, a familiar story for Tottenham fans. Liverpool scored early and late on to secure the title of European champions; Pochettino and his squad were left heartbroken and exhausted after the rollercoaster of a season.

The exhaustion of the squad was clear for all, especially manager Mauricio Pochettino, who stated he felt there needed to be a ‘painful rebuild’ at Tottenham.

The rebuild had already started that January as long term-servant of the club and midfield powerhouse, Mousa Dembele departed for the Chinese Super League.

Tottenham were looking to replace Trippier and Eriksen as well as Dembele in the summer. The rebuild started with Tanguy Ndombele joining for a club-record fee, while later in the window Giovanni Lo Celso and Ryan Sessegnon also joined for considerable prices.

Tottenham had spent for the first time in a season, and they had spent a large amount. It seemed to be looking like Tottenham could try and reach the next level following their Champions League heartbreak, with dreams of emulating Liverpool’s road to winning the Champions League; losing in the final the year before winning it.

However, everything didn’t go to plan at Tottenham, Pochettino found himself in a sticky patch that he struggled to pull out of, new signings failed to make an instant impact and Pochettino’s side just couldn’t win on the road.

After an emotional journey over many years, Levy decided to sack the Argentine manager, allowing Mourinho to take over as Tottenham’s new manager.

There was a time of turbulence in Mourinho’s first few months in the job as he managed to pull Tottenham up the table to a 6th place finish; however, Tottenham’s UCL final opponents last season, Liverpool, had only improved and clinched their first Premier League title; leaving Tottenham as the only ‘big six’ team left to not have been crowned the champions of England since 1992.

The start of the new season began to look promising for Tottenham as they had finally seemed to have found the funds to invest in the squad, bringing in six new players over the summer: the headline signing being bringing back Gareth Bale.

The optimism and hopes started to come into fruition in the first few months of the season as Spurs thrashed Southampton 5-2 away from home, then on October 3rd Spurs continued their free-scoring habits as they smashed Manchester United 6-1 away from home, on that very same day Liverpool were humiliated by Aston Villa as they lost 7-2 at the Villian’s home ground.

However, Liverpool managed to charge on and by December Tottenham found themselves parallel with the Reds once again, however this time it felt like it was going to be a turning point for either clubs’ season.

Spurs were top of the Premier League table by the 15th of December, ahead of Liverpool on goal difference, but the two sides were set to meet at Anfield on December the 16th; almost certainly deciding who would top the table by Christmas.

Salah and Son had been the goal scorers in the first half, creating a tense second half scenario, a tension that proved too much for Mourinho’s Tottenham as Bergwijn squandered great goalscoring opportunities and teed up Firmino to shatter Spurs fans’ dreams via a 90th-minute header.

Tottenham’s form was broken and chances to make this form building blocks for a rebuild were dismantled as Mourinho’s side weathered a troublesome few months; losing to Arsenal 2-1 and being turned over 3-0 by Dynamo Zagreb to be knocked out the Europa League within the space of four days flagged signs that Mourinho’s tenure at Tottenham was coming to an end.

Fast forward just over ten months and Antonio Conte is now at the driving seat of Tottenham, trying to drag the club by the scruff its neck in his traditional ruthless fashion, shipping out deadwood that he doesn’t trust as Dele Alli departed for Everton in January with two big-money signings also heading out the door in the form of Giovanni Lo Celso and Tanguy Ndombele.

But the main headline of the winter window would be how Tottenham fell short of attracting Luis Diaz to Tottenham, a player they had clearly desired and moved for but failed to attract to London as the Colombian chose Liverpool instead.

The Diaz scenario was a representative of Tottenham’s failures over the past years, directly contrasted by Liverpool’s successes.

Pochettino’s ‘painful rebuild’ has started: but not as the Argentine would have envisioned. Conte has seen his side suffer three losses to Chelsea, back-to-back losses against Southampton and Wolves at home and a defeat to Burnley, spelling out to the Italian the magnitude of the job he has on his hands.

But the recent impressive victories over Manchester City and Leeds are a sign of the levels Conte can take this team to, his character and managerial prowess is surely the type that Tottenham would need to drag them out of this slump.

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