A look at transfer windows in years gone by highlights that Tottenham aren't exactly fast movers when it comes to business.
Although Jack Clarke and Tanguy Ndombele did sign on the dotted line at the start of last July, Spurs fans had to wait until deadline day for Ryan Sessegnon and Giovani Lo Celso, who had both been heavily tipped to sign earlier in the summer, to complete their moves.
The Lilywhites tend to do most of their transfer business rather late on, as was the case in 2017 when all five of their summer additions joined in the final eight days of the window.
Everyone will be hoping things are rather different ahead of the 2020/21 campaign as Jose Mourinho and his squad look to hit the ground running.
Pierre-Emile Hojbjerg looks set to be the first summer addition at Tottenham Hotspur Stadium, with a couple more expected to follow before the transfer deadline at the start of October.
What Spurs must be this summer is decisive.
Expectations were incredibly high 12 months ago on the eve of the Premier League season following Spurs' run to the Champions League final a few months earlier, only for the campaign to turn out to be a complete disaster.
Despite Mauricio Pochettino bringing in four new players, his team couldn't build on their European heroics and in the end he paid for their poor start as he was relieved of his duties midway through November after some dire results.
Mourinho replaced him at the helm a matter of hours later and in the end managed to scrape Europa League football for the team after looking incredibly unlikely to qualify a few weeks earlier.
Finishing a staggering 40 points off Premier League champions Liverpool, Spurs have fallen so far behind some of their rivals this season and need to make it up incredibly quickly.
Perhaps paying for not strengthening at all in 2018/19 when their fellow top-six contenders did and moved ahead of them, the Lilywhites cannot afford to let the same happen once again or it could prove very costly indeed.
Daniel Levy and Mourinho need to be positive in the transfer window and get deals over the line swiftly.
Whereas the club did splash the cash one year ago with the likes of Ndombele and Lo Celso coming in, many will look back at the transfer window with regret given the constant links with Bruno Fernandes and Paulo Dybala.
The Portuguese international even admitted that he had agreed on terms to switch from Sporting CP but a deal never came to fruition as a fee couldn't be agreed on between the clubs.
Seen by many as a mistake at the time given his tremendous form in his native country, Fernandes only highlighted the point after reviving Manchester United's fortunes with 10 goals and eight assists following his January move to Old Trafford.
Dybala also had a very successful year in Turin as he was named Serie A's MVP after helping Juventus reclaim the Scudetto despite initial fears over his place in Maurizio Sarri's squad.
Both players could have totally transformed Tottenham's season and we could well be talking about a very different year altogether had Spurs managed to lure both to N17.
Spurs and the duo have now moved on and it's all about the here and now.
With additions needed in defence and a new striker to provide competition for Harry Kane, the club need to be active in the market and ensure Mourinho has all the right tools available to him so that the squad can get back to challenging at the top and for major honours once again.
Failure to do so and it could be another difficult year for everyone connected with Tottenham Hotspur Football Club.
