Daniel Levy has been Tottenham chairman since February 2001 and since then, he's overseen, orchestrated and administered almost countless incomings and outgoings at the north London club, always remaining a central figure in transfer matters.

And on the most part, it's hard to dispute with the work he's done. Tottenham's recent rise to Champions League finalists is often seen as Mauricio Pochettino's hard work alone but really, Levy's been at the epicentre of a transformation that's taken a whole lot longer.

Come the end of the first season in which Levy was at the helm, Spurs finished 12th. In the time since there have been peaks and troughs (fifth place in 2006/07 followed by 11th the year after, for example) but ultimately, Tottenham have been on a continuously upward trajectory throughout his tenure.

Much of that has indeed owed to Levy's dealings in the transfer market. His knack for buying young players, selling them on for considerably more and then reinvesting a fraction of the profits has worked a treat time and again.

A true test for any Spurs fan: Can you match these iconic images with the right results?

Levy secured massive markups on the likes of Gareth Bale, Michael Carrick, Luka Modric, Kieran Trippier, Kyle Walker and Dimitar Berbatov, while there have been plenty of incremental gains as well. Benjamin Stamboui was at Spurs for just one season and yet Levy still secured over £2m in profit on him.

But it hasn't always been smooth sailing and even the best at what they do make mistakes. Many will point to how Levy re-invested the Bale money in summer 2013, when Etienne Capoue, Roberto Soldado, Paulinho, Nacer Chadli, Vlad Chiriches, Erik Lamela and Christian Eriksen were brought in. Only the latter pair went on to any longevity at the club, the other five being little short of absolute flops.

But that summer, Levy at least made a profit of over £11m for Spurs and brought in Eriksen for just under £13m. He'd go on to make over 300 appearances for Tottenham, bagging 69 goals and 89 assists, before being sold this January at an eventual profit. Lamela is still at Spurs as well.

And that's the case with most of Levy's windows at Spurs. Whether it's simply the net spend surplus, like during the two transfer windows in which Tottenham famously signed nobody, or the odd gem amongst an otherwise uninspiring rabble of signings, there is usually always one or two positives to take from Levy's dealings.

But last summer remains a real exception to that as things stand, and may well go down as his worst ever transfer window at Spurs - not least because he veered so far away from the usual script, without anything of genuine note to show for it so far.

First and foremost, Spurs uncharacteristically produced a negative net spend of over £80m last summer, albeit somewhat justified by the fact they'd gone almost 18 months without signing anyone. But secondly and more important is the worrying lack of value for money within the cohort that arrived.

Of course, time may go on to paint a different picture, but the near £35m spent on youngsters Ryan Sessegnon and Jack Clarke doesn't look like good business akin to low-cost punts on the likes of Dele Alli or Walker, or even for that matter Kyle Naughton and Lewis Holtby.

Clarke has failed to make any sort of impression on loan at Leeds and QPR already this season, whereas Sessegnon has gone from making eight Premier League goal contributions at Fulham last term to starting just four top flight games for the Lilywhites, despite Tottenham struggling for bodies at left-back for most of the campaign.

But perhaps the even bigger concern is Tanguy Ndombele. Again, Levy broke usual habits by splashing out a huge £54m fee, but the big gamble hasn't paid off. He's been left with a club-record signing who's only been able to make 12 Premier League starts and appears to be completely at odds with his manager. Jose Mourinho has criticised him in public more than once, most recently after hooking him off at half-time against Burnley.

That leaves the loan swoop for Giovani Lo Celso as the only silver lining in Tottenham's summer, but even that remains somewhat tenuous considering he'd only made three Premier League starts before being signed permanently on January 28th. Really, the first half of the season was just an extended trial, one that actually cost more than £15m in loan fees. Again, hardly fantastic value for money considering they then paid another £27m to acquire him full-time.

No doubt, a lot can change in football very quickly. Clarke and Sessegnon could go on to become key figures at Spurs in the coming years, and Ndombele may well turn out to be a talent worthy of club-record status.

But as things stand, it's hard to see what Spurs have really gained from last summer's spending apart from a significant transfer deficit and a number of potential duds, and this was acquired with the added luxury of just reaching a Champions League final - something that should've given them extra pulling power in the transfer market.

Last summer has all the makings of being remembered as Levy's worst window for Spurs.