Tottenham's 4-0 aggregate thrashing by Leipzig added the misery of an early Champions League exit to a season in which the 2019 finalists have been brought crashing back down to earth.
A never-say-die spirit carried Spurs to the club's first-ever final in Europe's top club competition last year after memorable fightbacks at Barcelona, Manchester City and Ajax.
Faced with the same mountain to climb, there was nothing left in the Tottenham tank during a 3-0 defeat in Leipzig on Tuesday.
The comeback against Ajax in the semi-finals was arguably the high point of Mauricio Pochettino's five-and-a-half-year spell in charge that turned his team from Europa League regulars into Champions League contenders.
Less than six months after Tottenham's 2-0 defeat to Liverpool in the Madrid final, Pochettino was replaced by Jose Mourinho, and it appears even the Portuguese does not believe their run as a Champions League club will continue next season.
"With the squad we have at the moment it's going to be very, very difficult," said Mourinho, whose side sit eighth in the Premier League, seven points adrift of the top four.
"These problems are not going to disappear from today to tomorrow."
A run of six games without a win is the worst of Mourinho's long managerial career. However, there are mitigating circumstances.
The loss of Harry Kane and Son Heung-min to long-term injuries has robbed him of Tottenham's two main goal threats.
January signing Steven Bergwijn is also set to miss the rest of the season, while Moussa Sissoko has been a big miss in midfield.
"I think every team in the world would struggle with five or six of their most important players missing, it is as simple as that," said Mourinho.
"All the players that were on the Leipzig bench, in my team they would play."
Yet, it is hard to see how Mourinho's negativity is helping his squad to do any more than limp towards the end of the season.
"A broken team that under the joyless stewardship of Jose Mourinho has been broken still further," wrote the Guardian.
"They looked here exactly what they are: the eighth-best team in the Premier League, exhausted and error-prone, bad in defence and bad in attack, with no discernible long-term strategy and no identifiable short-term plan."
As Leipzig roared into the last eight for the first time in the club's history, Tottenham were offered a mirror image of what they once were in the peak years of Pochettino's reign.
The Germans are a young, hungry, energetic, exciting team led by one most coveted emerging managers in European football in Julian Nagelsmann.
Spurs are paying the price for not building on the foundations laid by Pochettino.
Not a single player was signed for 18 months between January 2018 and July 2019 that put a huge strain on a stretched squad.
Funds were finally released last summer but the Argentine was sacked just three months into the season after more than £100 million was spent on Tanguy Ndombele, Ryan Sessegnon and Giovani Lo Celso.
Even as Mourinho has bemoaned his lack of resources, Ndombele and Sessegnon have rarely featured, with the French midfielder receiving stinging public criticism from his coach after Saturday's 1-1 draw at Burnley.
Mourinho was keen to stress he does not foresee a summer overhaul in the transfer market.
"When we start (next season) we will have Sissoko, Kane, Son, Bergwijn and Ben Davies, so that is massive," he said.
But if they do not have Champions League football to look forward to, holding onto some of those stars and starting the cycle all over again will be a tougher task.
"Tottenham's current travails merely underline what a stunning job Pochettino did for those few magical seasons," added the Guardian.
That is little consolation for Spurs, who appear back where they started when Pochettino was appointed nearly six years ago.