Jamie Carragher assesses what has gone wrong for Tottenham, while Gary Neville looks at how Jose Mourinho could yet turn it all around.
"They are on a run of losing four out of five Premier League games and have just gone out of the FA Cup," Carragher told Monday Night Football.
"Jose Mourinho is a manager brought in to get results and if he does not get results there is not much behind it in terms of the spectacle or how they play. At times, we have lauded it. He is a results manager. And at this moment he is not getting results.
"It is fair to say that the top managers in Europe play a proactive game. Jose Mourinho is reactive. The top teams take calculated risks. Jose is risk-averse.
"What really stood out for me was watching Chelsea go to Tottenham and how they set up. This was Thomas Tuchel's third game in charge. Jose has been there 12 months.
"And Jose played that game to stop them.
"Going into that game, Chelsea were behind Tottenham and Tottenham were at home. It almost summed up the way we see managers right now and where Jose is.
"Steven Bergwijn and Tanguy Ndombele's job was to press or man-mark the opposition central midfield players. It was very narrow, something different just to stop Chelsea.
"It was really evident that this was Jose trying to do a job. It was not about hurting Chelsea, it was not about what we were going to do, it was about them.
"We are not saying that attackers should not defend, but it was almost like their job was to man-mark the opposition with no thought of how they were going to play themselves."
Tottenham lost to Chelsea as a result of Jorginho's first-half penalty, awarded after a foul by Eric Dier on Timo Werner. The error by the Spurs centre-back highlighted the fact that Mourinho is no longer working with defenders of the same quality as he had in the past.
"This is another point about Jose being reactive," Carragher explained.
"He has had success doing this. He would get in front - and I have played against his teams - and you are not even getting a draw. The draw was the best you were getting.
"At Chelsea, he had John Terry and Ricardo Carvalho. At Inter, he had Walter Samuel and Lucio, two of the best centre-backs you will ever see. Tottenham's defenders are nowhere near good enough, and neither is the goalkeeper, to hold onto leads."
Tottenham have conceded more points from winning positions than any other team in the Premier League this season - and the reactive approach has been a factor in that statistic.
"I can just think of two games off the top of my head - Wolves away and Crystal Palace away. Certainly, teams you would think Tottenham should be going for, looking for that second goal, trying to dominate. It just shows the manager that Jose is."
Will the ends justify the means for Spurs?
"But the big thing at the moment with Tottenham is this - Would winning the Carabao Cup in April justify the way that Jose Mourinho's teams play?
"The way that Jose's teams play, we know, Daniel Levy knows, the Tottenham supporters know that when he comes in. Does that winning a trophy justify being ninth considering that Tottenham did not win a trophy under Mauricio Pochettino?
"For me, you bring Jose in to keep what Pochettino was doing in terms of being around the Champions League places, there or thereabouts, but then just make that difference in a cup final or semi-final.
"But they are a long way away from the Pochettino team and I don't think that just winning a trophy justifies that if the performances carry on as they are and the league position carries on as it is. I don't think it does justify it.
"Pochettino was criticised for not winning a trophy and I get that. But we never think of Tottenham for the Premier League or for the Champions League, let's be honest. We might think that over 10 years they might win a cup.
"What Pochettino did that was special was that he made Tottenham supporters believe they could win the biggest trophies out there in terms of the Premier League and a Champions League final. That is what he did.
"So when people criticise him for not winning - and Pochettino used to say he was more interested in the big trophies than the little ones - that criticism for me was a little bit invalid.
"I do worry for Tottenham because I don't think they are good enough for the top four and I don't think they will get top four for that reason.
"I think they are a long way from being a top-four club and the way they are playing, you have to have results if you are going to play like that, and they are not getting them."
Neville: How Mourinho can turn it around
Gary Neville agreed that Tottenham are at a pivotal point in their season but made the argument that there is still a way that Mourinho can turn things around.
"I agree that this is an interesting moment," Neville told Monday Night Football.
"But in a month he has got a cup final so he could be a trophy winner. They are four points off the top four with a game in hand.
"He is in that moment in his Tottenham career where the next four or five weeks will determine whether we see what we have seen with Jose at his last couple of clubs or we see that, no, actually, he can change.
"He has got to bring Dele Alli and Bale round and I am not saying that he has to pander to these players because Gareth Bale has wound me up all season just watching him smile on the bench.
"Dele Alli, I worked with him for England, I think he is a brilliant talent but he should be doing a lot more. I want more from him. He is an outstanding player. Deliver on a great career. There is a reason why his career is going like this and it is not just Jose Mourinho, Dele has got to get over that himself.
"So for me, the Dele Alli and Bale situations need getting hold of and dealing with properly. That might mean that Jose Mourinho has not got the same control over top players that he had a few years ago when he was winning league after league and could do as he wanted or he will have to change how he deals with players.
"He will have to maintain good relations with the media and I think he is doing that at the moment, I think his interviews are good. He is going to have to win a few football games.
"But I don't think the style will change. The style that Jamie was criticising there is the style we were lauding earlier in the season when Harry Kane was dropping in and playing those balls in behind. It was not much different, he is just doing it without success now.
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"There is one more thing. They have just had Chelsea, Liverpool and Manchester City. The games are going to get a bit more comfortable in these next few weeks.
"That is why I think these next few weeks will determine whether they are on that Jose period where he starts to get a little bit disenfranchised or he could get hold of it, change the direction of it, get one or two players on side, win a trophy, get Harry Kane back in the team and play some easier games.
"We are in that moment of balance."