Jurgen Klopp and Jose Mourinho have previous.
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Klopp’s Liverpool host Mourinho’s United on Monday at Anfield (Watch live, 3 p.m. ET on NBCSN and online via NBC Sports) in a hugely anticipated clash.
Two of the best coaches in the game squared off five teams when Klopp was in charge of Borussia Dortmund against Mourinho’s Real Madrid and Chelsea.
Klopp has the undoubted edge over Mourinho, winning three of their five encounters and losing just once.
Here’s a look back at those games as the two as they prepare to face one another in the Premier League for the first time.
October 24, 2012 – Borussia Dortmund 2-1 Real Madrid: Robert Lewandowski and Cristiano Ronaldo traded goals in UCL group play but then Marcel Schmelzer scored the winner for Dortmund.
November 6, 2012 – Real Madrid 2-2 Borussia Dortmund: Pepe gave Real the lead but Dortmund went ahead through Marco Reus and an Alvaro Arbeloa own goal. Mesut Ozil’s late equalizer made it 2-2.
April 24, 2013 – Borussia Dortmund 4-1 Real Madrid: This was a classic Klopp demolition job. Lewandowski scored four times and despite Ronaldo’s equalizer, Real never looked in it.
April 30, 2013 – Real Madrid 2-0 Borussia Dortmund: Late goals from Karim Benzema and Sergio Ramos gave Real Madrid hope in the UCL semifinal second leg but Dortmund held on.
October 31, 2015 – Chelsea 1-3 Liverpool: Klopp helped to hammer one of the final nails in Mourinho’s second coffin at Chelsea. After Ramires put Chelsea ahead, two goals from Coutinho and a late clincher from Benteke did the damage.