1. Borussia Dortmund 4-1 Real Madrid (April, 2013)
Regarded as Klopp’s finest achievement in European football, to date. Borussia Dortmund stunned La Liga giants Real Madrid 4-1 in the first-leg of their UEFA Champions League semi-final back in April 2013. Poland international Robert Lewandowski became the first-ever player to score four times in a Champions League semi-final, with Cristiano Ronaldo’s second-half consolation proving nothing more than a mere consolation. Although late strikes from Karim Benzema and Sergio Ramos gave Madrid a 2-0 victory in the second-leg, Klopp guided the club to only its second-ever Champions League final after Dortmund won the elite tournament back in 1997. However, Klopp’s side eventually went onto lose 2-1 to arch-rivals Bayern Munich in the final at Wembley Stadium after Arjen Robben’s heartbreaking 89th minute winner.