Early exits in the League Cup and Champions League coupled with a steady, yet unspectacular, Premier League season leaves Spurs sitting in an awkward position.
The club is enjoying their greatest period of success in the Premier League era but are yet to win a trophy or make serious inroads towards a title/European success.
Mauricio Pochettino will no doubt ask for a war chest this summer to add the necessary quality to get Spurs to the next level but, for now, let's assess their performances this past season.
After being tipped as a contender for the title this season, Spurs found themselves out the running by December.
A 2-1 away defeat at Leicester on November 28th left the club in fifth place and 13 points behind eventual champions Manchester City.
11 wins from 14 after December 23rd assured Tottenham of a European place and the club qualified for the Champions League without much of a sweat.
Harry Kane was at his best again as he netted 30 goals while Son Heung-min proved to be their most impressive performer as he netted 12 times.
A third-place finish and the title of best team in London will give Tottenham fans reason to be happy but really there is a sense that Spurs should be taking that next step.
They did, however, possess the third best attack and third best defence.
Spurs strolled through their Champions League group and can look back at victories over Real Madrid and a double over Borussia Dortmund.
The last 16 draw cruelly pitted them against Juventus, but they looked like they could be heading through after securing an impressive 2-2 draw in Turin.
Back in London, Spurs managed to take the lead and looked like they were heading through, but two Juventus goals in three minutes broke their hearts and consigned them to an early exit.
FA Cup/EFL Cup
One of the main knocks on Pochettino’s Spurs record is the team's lack of trophies. The EFL Cup looked to be a trophy that the team would target ten years after they lost won it, but they surprisingly fell out of the competition in the fourth round thanks to a 3-2 home defeat to London rivals West Ham.
Worse for Spurs was that they actually led 2-0 at half time before the Hammers turned the game on its head in the second half.
The FA Cup proved kinder to Tottenham as they saw off AFC Wimbledon, Newport County, Rochdale and Swansea to make the semi-final.
With a perceived advantage of home turf, Tottenham could not overcome Manchester United despite taking an early lead through Dele Alli, Spurs lost the game 2-1 and all hopes of a trophy this season.
Highlight of the season
It has to be their victory over Real Madrid at Wembley. A perfect night for Spurs fans as two Alli goals and a Christian Eriksen strike led them to a 3-1 victory and sealed their place in the last 16 of the competition.
Spurs could also look back at their away draw against Madrid, their 1-0 win over Arsenal and even their 5-4 win over Leicester as highlights of the season.
Lowlight of the season
With Spurs leading 3-2 on aggregate and having two away goals with 30 minutes to play of their home leg against Juventus, surely they thought they were nearly home and dry?
It was a dagger to the heart then when Juventus turned the game on its head through Gonzalo Higuain and Paulo Dybala in just three minutes.
Spurs exited the competition and their fans could reflect on what could have been - especially because of Liverpool's heroics.
Final grade - B
No trophies and a disappointing Champions League exit will leave Spurs fans frustrated, but they can be happy with the team's progress and a third straight season at Europe’s top table is fantastic news.
Now they just need to give Poch some backing in the transfer window.
Did we miss anything? Let us know in the comments below.