Here we are again: another August, another unbalanced squad, a manager who knows he needs more, players unsure about their futures. It is a familiar problem at many clubs but at Tottenham, it feels particularly acute.

Few periods in football highlight the tension between the boardroom and the dugout better than the transfer window.

Whereas managers would like their squad for the season in place before the action starts, their chairmen and chief executives are often prepared to wait until the closing hours of the transfer window to try to conclude deals.

Tottenham chairman Daniel Levy does not have a public Twitter account, yet he might be proud to know that his transfer brinkmanship has its own hashtag — #levytime.

HOW LATE DEALS COST SPURS 2015-16

Form: LD

Players in: 1

Players out: 1 2014-15

Form: WWL

Pts behind CL place: 6

Players in: 2

Players out: 3 2013-14

Form: WWL

Pts behind CL place: 10

Players in: 3

Players out: 2 2012-13

Form: LD

Pts behind CL place: 1

Players in: 4

Players out: 4 2011-12

Form: LL

Pts behind CL place: 1

Players in: 1

Players out: 5 2010-11

Form: DWL

Pts behind CL place: 6

Players in: 2

Players out: 0 2009-10

Form: WWWW

Pts behind CL place: +3

Players in: 1

Players out: 2 2008-09

Form: LLD

Pts behind CL place: 21

Players in: 3

Players out: 2 2007-08

Form: LLWL

Pts behind CL place: 30

Players in: 0

Players out: 2 2006-07

Form: LWL

Pts behind CL place: 8

Players in: 2

Players out: 0 2005-06

Form: WWDL

Pts behind CL place: 2

Players in: 3

Players out: 2 *Above shows Tottenham’s form and transfer dealings between start of the season and the end of the transfer window - and how many points they finished behind a place in the Champions League

But by leaving it so late to complete business, does Levy risk damaging the club’s chances of achieving his primary goal — Champions League football? Between 2010-11 and 2012-13, Spurs won just one of their seven League games in August as first Harry Redknapp and then Andre Villas-Boas worked with squads still under construction. In two of those three seasons, they finished only one point outside the Champions League places.

This season Liverpool and Spurs were named as contenders for a top-four spot. After two games, Spurs are already five points behind Brendan Rodgers’ side. Can anyone spot a pattern?

If players like Emmanuel Adebayor, Scott Parker and Hugo Lloris, to name three, had been signed at the start of August, Spurs would surely not have missed out as they did. It is the same with player sales. By leaving final negotiations until late in the window, Levy was able to extract maximum price for Dimitar Berbatov, Luka Modric and Gareth Bale — but at what cost?

To hold out for a better deal in this way risks weakening the club in the long run, as no Champions League means no huge television revenues. Less money coming in makes it more difficult to sign the players who can deliver the main prizes.

As Mauricio Pochettino admitted last week, Spurs are looking for potential in the transfer market, rather than proven footballers, at a time when the head coach believes he needs more experience.

Yet this evidence is not enough to persuade Levy to change his ways.

Levy made his intentions clear in July when, in a rare interview, he predicted that “the activity will happen in the last two weeks”. Tottenham supporters are frustrated at Levy’s summer strategy but they should know this: Levy’s priority is the deal and he enjoys negotiating. That means certain players will be signed and sold against the wishes of the manager.

One club chief tells a story of being summoned by the Tottenham hierarchy a couple of summers ago, to be presented with a list of players Spurs were prepared to sell. He left unsure about whether the Spurs manager at the time had given the list his blessing.

Here are two examples of this conflict: in Benjamin Stambouli, supporters see a mystifying signing who lasted less than a year at the club before moving on. Levy sees a player bought for £4.7million and sold for £6m. It is the same with Lewis Holtby, the German midfielder signed for a small fee in January 2013 and sold to Hamburg for £6m this summer.

Tottenham's new stadium - In Pictures 6 show all Tottenham's new stadium - In Pictures 1/6 Capital gains Spurs hope to create a thriving and exceptional sports, leisure and entertainment destination in Tottenham Tottenham Hotspur FC 2/6 World class arena The stadium will be the finest anywhere in the world, pledge Spurs Tottenham Hotspur FC 3/6 Top of the world A 'Sky walk' will allow visitors access to stadium roof Tottenham Hotspur FC 4/6 Job creation Once complete Tottenham will go from supporting 1,800 jobs to supporting 3,500 in the area Tottenham Hotspur FC 5/6 A whole new ball game The new venue will host at least two money-spinning NFL games a year for a decade Tottenham Hotspur FC 6/6 Ground force The new stadium will include the largest single tier stand in the UK, now increased to 17,000 seats. Tottenham Hotspur FC 1/6 Capital gains Spurs hope to create a thriving and exceptional sports, leisure and entertainment destination in Tottenham Tottenham Hotspur FC 2/6 World class arena The stadium will be the finest anywhere in the world, pledge Spurs Tottenham Hotspur FC 3/6 Top of the world A 'Sky walk' will allow visitors access to stadium roof Tottenham Hotspur FC 4/6 Job creation Once complete Tottenham will go from supporting 1,800 jobs to supporting 3,500 in the area Tottenham Hotspur FC 5/6 A whole new ball game The new venue will host at least two money-spinning NFL games a year for a decade Tottenham Hotspur FC 6/6 Ground force The new stadium will include the largest single tier stand in the UK, now increased to 17,000 seats. Tottenham Hotspur FC

Levy knew that Stambouli and Holtby could be resold at a profit, thus improving Spurs’s financial position. Hence his anger at how the £86m fee for Gareth Bale was used in the summer of 2013. Four of the seven players who arrived two years ago have left, all at a loss. Levy pinned most of the blame on Franco Baldini, and the Italian will leave his post as technical director at the end of the month. Levy has strong arguments to defend himself. He can point to a club in a healthy financial position. He can present the plans for the new stadium he hopes will take Spurs into the elite. He can show a record of a club which has finished in the top five in five of the last six seasons, thanks partly to his work in the market.

Yet as Levy attempts to tie up deals for a forward and a midfielder before the transfer window closes, Spurs seem to be drifting away from the top four, not gaining ground. If Levy is familiar with the work of 19th-century philosopher George Santayana, he will know this warning: “Those who cannot remember the past are condemned to repeat it.”