Tottenham travel to Leipzig on Tuesday needing to overturn a 1-0 first leg deficit to prevent adding an early Champions League exit to a season spiralling out of control.
Saturday's 1-1 draw at Burnley stopped the rot of four consecutive defeats in all competitions that has seen Jose Mourinho's men fall behind in the race for a top four finish in the Premier League and eliminated from the FA Cup by bottom-of-the-table Norwich.
Failure to fight back in Germany will also halt the progress Spurs have made in the Champions League in recent years.
Under Mauricio Pochettino, Tottenham went further in the competition for each of the past three seasons, culminating in a rollercoaster run to the final last season.
Rather than using defeat in Madrid to Liverpool last June as a springboard to continue competing with the European elite, Spurs have unravelled.
Pochettino was sacked just three months into this season after five-and-a-half years in charge that transformed the club's fortunes.
Rather than follow the template of Pochettino's appointment with a young and forward-thinking coach like Leipzig's Julian Nagelsmann, Spurs chairman Daniel Levy was wowed by Mourinho's past.
The Portuguese has 25 trophies to his name, but the last of them came three years ago and recent spells at Chelsea and Manchester United did little to suggest he was the man to take Spurs forward.
So it has proved with Mourinho's negativity contributing to the gloom around the club.
After losing Harry Kane and Son Heung-min to injury, Mourinho has repeatedly stated the end of the season cannot come soon enough.
Levy's big call
The 57-year-old is quick to bemoan his lack of resources at what is now the eighth richest club in the world, according to Deloitte's Football Money League.
However, he was scathing of Tottenham's club record signing Tanguy Ndombele after hooking the French midfielder at half-time on Saturday.
"My thinking was that in the first half we didn't have a midfield. Simple as that," he said.
"I'm not going to run away and I have to say that Tanguy had enough time to come to a different level.
"I know that the Premier League is very difficult. For some players, it takes a long time to adapt to a different league, but a player with this potential and responsibility has to give us more than he is giving us."
Mourinho dressing down an underperforming star player in public is nothing new, but evidence from his previous clubs suggests it does little good.
At 23, and in his first season in England, it is questionable as to whether Mourinho's criticism of Ndombele is the best way for Spurs to realise the potential of their €63 million signing.
Levy also has to bear his share of the blame for Spurs' decline.
As he oversaw a 1 billion project for the club's new stadium that ran well over budget and time, he allowed Pochettino's squad to stagnate without a single signing between January 2018 and August 2019.
At the same time, Levy demanded exorbitant fees for players that could have been sold to reinvest in the squad and saw many of those assets depreciate. Christian Eriksen was sold to Inter Milan in January for a cut-price 17 million with just six months left on his contract.
Levy faces another crossroads come the end of a season that Mourinho so desires.
Does he back his bet on an experienced coach by meeting his demands in the transfer market, or cut his losses on a coach he signed until 2023 in November on a reported €15 million a year?