Mauricio Pochettino has plenty to think about.
And plenty of work to do on the training field, too.
After coming from behind to beat Aston Villa and picking up a lucky point away at Manchester City, it was a first defeat of the season on Sunday as they lost to Newcastle United.
Spurs were poor from start to finish and go into next weekend's North London Derby on the back foot.
There are questions behind the scenes that need answering too.
Here we take a look at the biggest stories from the world of Tottenham from the past 24 hours.
August woes
Victory over Aston Villa, having come from behind, a draw away at Manchester City and defeat to Newcastle United.
It has not exactly been a month to write home about for Tottenham.
Mauricio Pochettino has been complaining about what's been going on behind the scenes, with players' futures still up in the air, given the September closing of the European transfer window.
But why has it been so troublesome?
Jack Clarke's Leeds problems
Jack Clarke became Tottenham's first new signing in three windows when he joined the club this summer.
But he immediately went back on loan to Leeds United for the season.
Was that a good move, however?
The teenager has yet to play a minute of Championship football this season, with loan rules restricting his involvement.
Here we take a look at the problems he and Spurs are facing.
Players to leave
The European transfer window remains open until September 2, much to Mauricio Pochettino's chagrin.
There are questions marks over a number of his current players, with the boss saying it has been "unsettling".
Focus on the pitch needs to be on this weekend's huge clash with Arsenal in the North London Derby - with added importance on it with Spurs having lost 1-0 to Newcastle at the weekend.
We take a look at the players who could have left the club before that game even comes around.
Penalty verdict
Harry Kane thought he should have been given a penalty on Sunday.
In fact, most of the Tottenham fanbase felt he should have had a penalty.
The Spurs striker was almost rugby-tackled to the floor by Jamaal Lascelles during the shock 1-0 defeat to Newcastle at Tottenham Hotspur Stadium.
But referee Mike Dean did not award a penalty and VAR did not feel the need to intervene either.
Toby Alderweireld's future
Will Toby Alderweireld still be a Spurs player next month?
Will he still be a Spurs player next year?
The Belgian is out of contract next summer and will be free to leave N17.
But are Spurs willing to offer him new terms on a new contract?
.png?w=600)
