Tottenham Hotspur have lots to do in the transfer window this summer as they look to get back in the mix for a Champions League place. A number of incomings and outgoings must take place in order to give Ange Postecoglou the best squad possible to compete towards the top of the Premier League.
As is the case every transfer window, fans will be hoping that the club spend a good amount of money and sign some top players in the process. Things don't always turn out like that, however, with many Spurs supporters pointing at the club's failures in the transfer market in the past.
Here we take a look at what a nightmare transfer window might look like for Postecoglou and Tottenham.
Maddison opts for Champions League football
One player who has been mentioned in regards to a switch to Tottenham this summer is James Maddison. The Leicester City man will depart the King Power Stadium ahead of the summer transfer deadline following the Foxes' relegation to the Championship and also because the club need to cash in on him due to his contract status.
Tottenham aren't the only club looking at the England international as Newcastle United are also targeting the 26-year-old. Eddie Howe's side do have Champions League football to offer the attacking midfielder, which could potentially prove decisive in the race to sign him and duly hand Spurs a hammer blow in the process.
READ MORE: Alex Scott, Germany international and transfer bargain Ange Postecoglou and Tottenham could sign
Kane exits
Talk over Harry Kane's future has dominated the back pages in recent months as he nears the final 12 months of his Tottenham contract. Linked with a mega-money move to Man United, reports last week claimed that the Red Devils have now ended their interest in the England captain due to how much money it would take to prise him away from north London.
Real Madrid were also in the headlines recently regarding a move for Kane following Karim Benzema's exit, although talk of a switch to the Santiago Bernabeu has also died down. Now odds-on to remain at Tottenham next season, all fans will be hoping there is not a late twist in the tale towards the end of the transfer window.
That would come as a major blow to Postecoglou and leave Spurs with a huge challenge in somehow trying to replace a man who offers the team so much in the final third.
Centre-back failure
The main priority at Tottenham this summer is to strengthen at the back after leaking goals for fun last campaign. The 63 league goals they shipped was a major reason for missing out on European football altogether and there must not be a repeat.
There really needs to be a complete overhaul at the heart of defence and Tottenham ideally need to bring in a new centre-back on the same level as Cristian Romero. Another centre-back will also be required, with another one possibly even needed depending on what happens with outgoings.
Failure to do that and it could make things rather tricky for Postecoglou in his first season at the club. Daniel Levy and Spurs need to give the Australian the best possible tools to do his job as that's the only way Tottenham will get back on track and flourish once again.
Who would you keep or sell at Spurs this summer? Have your say below!