This week, they face Red Star Belgrade in the Champions League and will be hoping to add to the solitary point they've taken from their opening two games.
Harry Kane may still be scoring goals, with seven in 11 games, but the team as a whole needs a lift.
The Spurs captain believes it is a challenge that the squad must overcome in order to match the high standards they've set in recent years.
"Yeah, probably, I’d say [this is the toughest spell at Spurs]," he said (as reported in the Evening Standard).
"When you look at the results it’s not been easy. Of course we all want to be winning games. The manager wants to be winning games.
"It’s another challenge, another challenge in my career, the club's time and team's career. It's about trying to overcome that. It’s not going to be a straight path to success.
But Kane does believe that a win against Red Star will be a boost that might help lend some perspective to Spurs current situation.
"If we can win tomorrow night it will put us in a better position [in the Champions League] than last year and we ended up going to the final," he added.
"We have to believe and every game fight and fight for each other and who knows what’s possible.
"It is important to start well, come out of the blocks with loads of energy, with and without the ball, and try and get ahead and win the game.
"It is important for us as a team to stick together, keep working hard, doing our best on the pitch and hopefully we can win tomorrow and it can kick us on to another winning run."
Tottenham face Red Star Belgrade on Tuesday night in the third round of matches in the Champions League group stage.
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