Liverpool’s Champions League clash against Napoli on Wednesday night will see Jurgen Klopp reach a century of European matches in his illustrious managerial career.
The German has, more often than not, experienced success in continental competition with his most notable triumph arriving last season when he guided the Reds to Champions League glory in Madrid.
His European success has not been limited to Merseyside though. Klopp’s Borussia Dortmund also provided several memorable moments during his seven years at the helm and it was at Mainz that he first experienced football outside of Germany as a coach.
Jurgen Klopp will take charge of his 100th European match as a manager on Wednesday night
His greatest night in Europe came in June when his Liverpool side won the Champions League
There has been heartbreak, too. Klopp has lost three finals, two in the Champions League — against Bayern Munich (with Borussia Dortmund) and Real Madrid (with Liverpool) — and another with Liverpool in the Europa League against Sevilla.
His journey into Europe started in July 2005 when Klopp led Mainz into the UEFA Cup via the Fair Play League and the reward was a date with FC Mika of Armenia.
They made light work of them and progressed to the next qualifying round where they also breezed past Keflavik of Iceland. Their reward was a first-round tie against Sevilla but the Spaniards proved too strong and Mainz were eliminated.
Klopp arrived at Dortmund in the summer of 2008 and his debut season in Europe ended in a penalty shootout defeat by Udinese in the first round of the UEFA Cup. He had to wait until 2010-11 to return to European football, leading Dortmund to group stage elimination in the Europa League.
His first experience in Europe came back in 2005 when he led Mainz into the UEFA Cup
He led Dortmund back to the Champions League group stages for the first time since 2003-03 in the following campaign but again could not get past the group stage, losing four of his six games.
The following season, 2012-13, would prove to be his most successful with Dortmund as their energetic brand of football and the goals of Robert Lewandowski saw them go all the way to the final, which they then lost to Bayern thanks to Arjen Robben’s late winner at Wembley.
A quarter-final exit in 2013-14 and failure to make it past the last-16 in 2014-15 were disappointing results for his final few years in Germany but Klopp’s record at Liverpool has been almost perfect.
Less than a year into his post at Anfield, Klopp led Liverpool to the Europa League final. He would suffer more disappointment though as Sevilla came from behind to beat his team 3-1 in the final in Basel.
The absence of European competition in 2016-17 helped the Reds in their quest to qualify for the Champions League the following season and they secured a top-four place on the final day of the campaign.
The arrivals of Mohamed Salah and Virgil van Dijk, as well as some sensational attacking performances, helped Liverpool unexpectedly qualify for the final in Kiev. A nightmare for goalkeeper Loris Karius against Real Madrid consigned them to defeat and another final loss was added to Klopp’s record.
He finally managed to become a European champion in June though when his side beat PSG, Napoli, Bayern Munich and Barcelona en route to the final, before overcoming Tottenham in Madrid to win Liverpool’s sixth European Cup.
Klopp then started this season with his fifth European final, beating Chelsea in Istanbul to win the UEFA Super Cup.
Klopp celebrates with his Dortmund players on their way to the 2013 Champions League final
Dortmund suffered heartbreak at Wembley though, losing to Bayern Munich late on in the final
Victory on Wednesday night against Napoli will see Liverpool advance to the last-16 but how does Klopp’s European record stand before his 100th game? He has won 52 of his 99 so far, drawn 22 and lost 25, giving him a win percentage of 52.5.
His teams have scored 188 goals in those 99 matches and conceded 110. Both of his heaviest victories in Europe have come as Liverpool manager, beating Spartak Moscow and Maribor 7-0 in 2016-17 and 2017-18 respectively.
His biggest defeats are four 3-0 losses. One came in last season’s Champions League semi-final first leg against Barcelona, before their dramatic comeback at Anfield, while the other three came in charge of Dortmund against Juventus, Real Madrid and Marseille.
Klopp has faced Real Madrid and Sevilla more than any other club across the continent, taking on each side seven times. He has the best record against Manchester City and Real, chalking up three wins against both.
In terms of managers he has faced, Klopp has gone head to head with Arsene Wenger the most. He has played the former Arsenal boss six times, beating him on two occasions.
Sergio Conceicao, former manager of Porto, is the man he has beaten more often than not after racking up three victories in the last-16 in 2017-18 and the quarter-finals last season.
Klopp will come up against Napoli for the sixth time on Wednesday night and will be looking for his third win against the Italian giants. Carlo Ancelotti is also a frequent adversary, they will meet for the sixth time tonight, and Klopp hopes it will be him celebrating on his special anniversary.
Klopp and his Liverpool players pictured after their dramatic win over Barcelona last season
The Liverpool players launch Klopp into the air as they celebrate their Champions League win