After failing to reach the Champions League last term the hope was that the Premier League side would prove their elite quality this term.
Manager Nuno Espirito Santo has already been sacked, there's been heavy defeats to Manchester United and Chelsea while the Europa Conference League defeat to NS Mura was a real low point.
The most disappointment aspect of this season, however, has been the form of Harry Kane.
The England skipper endured a disrupted summer with ongoing links over a move to Manchester City seemingly hampering the opening weeks of his season, however few would have predicted that his barren spell would continue into December.
Despite scoring seven in cup competitions, Kane has been limited to just one Premier League goal, an effort that came in mid-October against without-a-win Newcastle United.
Since Antonio Conte has come in there's no doubt that Spurs look like a more solid unit, but the mystery around Kane's form is yet to be solved.
The 28-year-old is almost exclusively known as the man to make Tottenham tick, but in actual fact it's one of his teammates who is the more influential player.
Son Heung-min is regarded by many as the Robin to Kane's batman, but when it comes to goal involvements on home turf he's actually much higher.
Since moving to the Tottenham Hotspur Stadium, the South Korea international has been directly involved in more Premier League goals than any other player with a tally of 34 (19 goals, 15 assists).
Son's effort against Brentford on Thursday night was his 75th in the Premier League, a tally that is bettered by just four players in Tottenham history (Harry Kane 167, Teddy Sheringham 97, Jermain Defoe 91, Robbie Keane 91).
No one would claim that the pacy forward is a more prolific frontman than Kane - the reality is that on his day, only a handful of players can get anywhere near matching him.
However if Conte is looking to add vital consistency to his ranks as they go in search of a top four finish then perhaps the need for Kane to find his scoring boots isn't quite as essential as many think.
The solution to Tottenham's problems may already be in place in the first team side and so the challenge must be in trying to ensure that Son is able to rack up his consistent numbers on a long-term basis.
If he can then the North London side might just surprise a few this season.