Antonio Conte's side suffered a disappointing 1-0 defeat to Middlesbrough in the FA Cup on Tuesday, their last chance of ending their almost 14-year trophy drought this season.
After a 4-0 victory against Leeds on the weekend, Tottenham travelled to the Riverside Stadium in an attempt to reach the quarter-final of the cup competition.
The form since the Italian's arrival has been up and down and this inconsistency continued with Spurs' performance and result against the Championship outfit.
The Lilywhites' last hope of some success this season is a top four finish and they are currently five points off fourth-placed Man United, with two games in hand, but there is still a lot of work to do to secure the Champions League place.
In the January transfer window Tottenham saw four first team departures and just two arrivals, despite Conte wanting a right wing-back, central midfielder and striker.
The decisions regarding the transfer business didn't put Spurs in the strongest position possible to help them have a successful final few months of the season.
Lack of incomings, along with a number of injuries, have left gaps on the bench which academy players have filled - a great opportunity for them but perhaps showing the lack of depth in the squad that Spurs have, although the Italian denies this.
"No, no, no. I don’t give a gift to my players, even if you’re 17 years old," Conte admitted ahead of the FA Cup tie. "I think Dane [Scarlett] is working hard, he is a really good prospect from the academy."
The summer transfer window will be a pivotal time for Spurs as they will need to do business which will help them make the step-up required, ahead of the 2022/23 season.
Tottenham's recruitment has previously been criticised and Conte has already spoken about the reason behind the new arrivals being brought to N17.
"[Rodrigo] Bentancur and [Dejan] Kulusevski are ideal prospects for Tottenham because the club is after young players who can improve and develop, rather than players who are the finished article," he admitted. "That's the story here. That's the link. That's the club's vision and philosophy."
The 52-year-old has admitted he likes to have players with experience in his side, which not all of Tottenham's young players have.
This is why the summer will be vital in backing Conte's ideas and helping him create the strongest possible squad.
Decisions off the pitch need improving but those on the pitch also need to change.
Tottenham had 15 shots against Middlesbrough and six on target, which should've been enough to get the lead but with six offsides, it ended in disaster for Spurs.
On a number of occasions, Conte's players should've passed the ball instead of shooting or should have, in fact had a shot rather than pass.
Some of this may come down to the lack of confidence in players, which could be down to several factors, but that doesn't help their side in moments when chances need to be taken and converted into goals.
Against Middlesbrough, there was an opportunity when Joe Lumley came out of his goal and Matt Doherty decided to have a shot, but if he had squared it to Son Heung-min, there may have been a better chance to score.
Son had a number of opportunities throughout the game but in his chance in the final minute, he may have benefited from controlling it with his chest and then having a shot, rather than going straight in to head it.
There were also a number of occasions where Spurs played the ball at the back and were passing it to Hugo Lloris, putting the shot stopper under unnecessary pressure.
There is no way of knowing if these different decisions would've changed what happened in the game, but it isn't just against Middlesbrough when the wrong choices seem to have been made.
As the game went on there seemed to be a lack of urgency from the Tottenham players who were running out of time to come out on top and it was in these circumstances when they should've given everything to get it up the field.
This did happen but there were also times when they decided to play it backwards rather than forwards, which has been a criticism of the Lilywhites in a number of games.
It isn't just decisions on the ball that are often poor, off the ball a number of players don't find good enough space to receive the ball.
In recent games, some are caught ball watching when Spurs are both in and out of possession and it means a lack of options for Conte's side when they are looking to play the ball, which is also why some bad decisions are likely being made.
Defensively, when the opposition are attacking the Lilywhites need the whole side alert and ready to defend and then if the opportunity comes about, break and go on a counter attack.
There are moments in games when Tottenham do this and can do it well but it all, again, comes down to inconsistency and that it doesn't happen often enough.
This is why outgoings are arguably just as important as incomings during the summer window.
If Conte's influence can't improve players enough by the summer then an exit may be what is best for both them and the squad.
Playing quick football with all players alert for 90 minutes, everyone looking for space and ways they can help their squad with the next move is something that most of the Tottenham players need to improve on and if they don't, there won't be much of a surprise if some more poor results are to come in the final months of the season.
