Just 111 days into his reign as Tottenham boss, the Special One is already facing judgement day.
Jose Mourinho faces a huge test in the competition which first made his name but now he must prove it all over again with his reputation on the line.
Tottenham are out of the FA Cup, face a huge task to get into the top four and going out of the Champions League at the first hurdle in the knock-out stage would end any hope of winning silverware this season.
It would increase the negativity swirling around Mourinho who was brought in because of his proven track record but always faced a thankless task to follow Mauricio Pochettino who was adored by the fans.
This is Mourinho’s moment, the chance to shine and endear himself to the Tottenham supporters but, amid a crippling and growing injury list, the task could not be much harder.
Tottenham trail from the first leg, do not have a fit centre forward and even their new £26m January signing Steven Bergwijn has been ruled out for the rest of the season.
But now Mourinho must mastermind another huge European result, the sort he achieved at Porto, led Inter Milan to glory against the odds and even won the Europa League with Manchester United .
No wonder perhaps Mourinho tried to turn the pressure on RB Leipzig who start as big favourites even if the Portuguese smiled and laughed his way through the pre-match press conference to try and prove he is not weighed down by the pressure.
“I’m very motivated, very calm, very positive but if you want to imagine Leipzig without Werner Schick, Nkunku, Poulsen, Forsberg, I am pretty sure the coach wouldn’t be laughing as much as I am now. Not easy," he said.
“It’s not often a defeat leaves the door open. Of course we prefer to be in their position but I believe they will feel the pressure. They are winning and we are going to have a go and have nothing to lose.
“We feel hurt by the fact we recovered 11 points in short period of time to the fourth position in the Premier League and then arrive in to a situation where we are really, let’s say, in trouble.
“Momentum is negative in this moment in terms of results. We lost and drew and one of the draws ended in defeat in the FA Cup on penalties. So momentum is not the best but the boys deserve something special.
“I think we fought really hard against all the circumstances and the boys deserve this kind of happiness that a victory in knock-out in the Champions League can bring.”
Mourinho has won the trophy twice so it is always hard to make comparisons but this is a manager who has been capable of achieving incredible one-off results. He will need another one in Leipzig.
But Mourinho believes his players have the mental strength and attributes to get a result, although he says one-off wins will never compare with actually lifting trophies which goes back to his first target as Spurs boss.
“The achievements that stay for ever are the victories. Of course would be amazing to do it but when you lose a final you throw the medal away and forget. Less than winning is not a big achievement. My big achievement in this competition is when we won,” he said.
“Defensively we feel the pressure and every time we make a mistake it looks like we’re punished. Boys are not silly. They understand. But when we understand opponents we don’t hide our fragilities and problems.
“We have to be together to have a fantastic individual performance to make our collective responsibilities very solid. I believe in the boys and I think we can make it.”
