Erik Lamela, Lucas Moura and Harry Kane put Spurs in control before league debutant Juan Foyth gave away two spot-kicks, converted by Ruben Neves and Raul Jimenez. The Euro Club Index estimates the chance of progress for Spurs at around 15%.
The game would end in a 2-1 win for Tottenham, a result which keeps them in the mix for a place in the Last 16.
Tuesday's narrow success was Tottenham's first in the group stage and leaves them three points behind second-placed Inter Milan and six adrift of leaders Barcelona with two fixtures remaining.
For the last few seasons Liverpool have leapfrogged their Manchester rivals in terms of challenging for silverware and while Jose Mourinho has been struggling to recapture the glory days of Sir Alex Ferguson at Old Trafford, Jurgen Klopp has helped produce one of the finest teams in Europe, who made it to the Champions League final last season.
"If we can play with that intensity, move the ball quickly, we'll get some chances and hopefully, we'll take some".
Alli lost another duel with Zoet soon after, this time watching in despair as the Dutch keeper pushed away his low drive.
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Their vulnerability from set-pieces was again exposed as De Jong, who scored PSV's late equaliser in Eindhoven a fortnight ago, out-jumped everyone and planted a firm header into the corner from Gaston Pereiro's corner.
"Today [his job] was to play alone like a holding midfielder, with Christian [Eriksen] and Dele Alli next to him".
PSV's resistance was finally broken Kane found the bottom-right corner with a left-footed strike following a Fernando Llorente knockdown. There was more to come from the England striker.
"Pleased of course, we're always trying to improve, but with all the circumstances the team is fighting".
Here, we use Opta data to dig a little deeper into Tottenham's Premier League form to see what the underlying causes of Pochettino's unhappiness could be.
"We have the character of never giving up which is so important".
Tottenham host Inter in Gameweek 5 and Mauricio Pochettino can be confident of claiming an all-important win.