The German has enjoyed considerable success at Mainz, Borussia Dortmund and at Anfield.
He has been able to make his teams competitive and difficult to break down, but the floodgates were blown open at the Etihad Stadium on Saturday.
The first-half dismissal of Sadio Mane for catching City goalkeeper Ederson in the face with a high boot ended up costing the Reds dear, as they slipped to a crushing Premier League defeat.
Mane’s red card unquestionably altered the course of the game, with Liverpool having looked threatening up until that point.
They were, however, unable to contain a City side blessed with enviable attacking options once reduced to 10 men.
Klopp’s side already trailed to Sergio Aguero’s opener when seeing Mane head down the tunnel, with Gabriel Jesus and Leroy Sane going on to bag a brace apiece to compound their misery.
Liverpool are next in action on Wednesday when they open their Champions League group stage campaign at home to Sevilla, before welcoming Burnley to Anfield in domestic competition next weekend.
