Tottenham Hotspur face an uphill task after being beaten at home by RB Leipzig in the first leg of the UEFA Champions League 2019-20 round of 16.
The German club emerged 1-0 winners in London.
Meanwhile, Italian side Atalanta, who made their UCL debut, overcame Valencia 4-1 at home.
Here are the records scripted.
In his UCL career, Spurs boss Jose Mourinho went on to the first leg of a Champions League knockout tie at home for only the third time.
The Portguese also became the fourth manager to take charge of 150 UCL matches after Sir Alex Ferguson, Arsene Wenger and Carlo Ancelotti.
Meanwhile, Tottenham are the sixth side Mourinho has managed in the UCL knockout stages.
RB Leipzig had 12 shots during the first half. This is the most they have ever had during the opening 45 minutes in an away Champions League tie.
Leipzig manager Julian Nagelsmann (32 years, 211 days) became the youngest person to take charge of an UCL knockout match.
Timo Werner's first seven UCL goals for RB Leipzig have come away from home.
Atalanta, who became the first team to qualify for the last 16 after losing their opening three group games, staged a remarkable victory to have one feet in the quarters.
Out of five shots on target, the Italian side scored four against Valencia.
Hans Hateboer scored Atalanta's first ever goal in the knockout stage of the competition.
Spurs have a mountain to climb in Germany against a well drilled Leipzig side.
With no notable strikers in the side, it will be difficult for Mourinho and his men.
Rotating the squad and managing this difficult phase will be key.
Meanwhile, Atalanta will be wary of Valencia in the second leg.
They have a big advantage, however, nothing can be taken for granted.
⏰ RESULTS ⏰⚫🔵 Hateboer (2), Iličić Freuler net for #UCL debutants Atalanta 🔴⚪ Werner converts spot kick as visitors Leipzig win in London🤔 Best moment tonight?#UCL— UEFA Champions League (@ChampionsLeague) February 19, 2020
⏰ RESULTS ⏰⚫🔵 Hateboer (2), Iličić Freuler net for #UCL debutants Atalanta 🔴⚪ Werner converts spot kick as visitors Leipzig win in London🤔 Best moment tonight?#UCL
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