Jurgen Klopp's wait for a major trophy goes on following Liverpool's 3-1 defeat to Real Madrid in Kiev.
The German has contested seven cup finals as a manager - four at Borussia Dortmund and three with Liverpool - but only won one of them.
2012 German Cup - Borussia Dortmund 5-2 Bayern Munich - WON
Klopp reached the first cup final of his managerial career in 2012, when his Borussia Dortmund side, who had wrapped up the Bundesliga title a few weeks earlier, dismantled a star-studded Bayern Munich 5-2 at the Olympic Stadium in Berlin to lift the German Cup.
Shinji Kagawa's third-minute opener was cancelled out by Arjen Robben's penalty, but Mats Hummels put Dortmund back in front from the spot, with Robert Lewandowski completing a hat-trick after Franck Ribery had netted Bayern's second.
2013 Champions League - Borussia Dortmund 1-2 Bayern Munich - LOST
The 2012/13 season ended on a disappointing note for Borussia Dortmund and Klopp as they suffered an agonising defeat to their old foes Bayern Munich in all-German Champions League final at Wembley.
It was a pulsating encounter with chances for both sides. Mario Mandzukic put Bayern ahead on the hour mark, but Ilkay Gundogan pulled Dortmund level from the penalty spot after Dante, who was fortunate not to be sent off having already been booked, caught Marco Reus in the stomach. Robben then struck Bayern's winner two minutes from time, latching onto Franck Ribery's flick and beating Roman Weidenfeller to break Dortmund's hearts.
2014 German Cup - Borussia Dortmund 0-2 Bayern Munich (aet) - LOST
Klopp suffered more heartache against Bayern Munich in the 2014 German Cup final. His Dortmund side had beaten Pep Guardiola's men 3-0 in their previous meeting in the Bundesliga just a few weeks earlier, but there was no repeat of those heroics back at the Olympic Stadium in Berlin.
The game, notable for Lewandowski's return to Dortmund's starting line-up despite the fact he had already agreed to join Bayern, was goalless after 90 minutes but ended in a 2-0 defeat as Robben and Thomas Muller struck in extra time.
2015 German Cup - Borussia Dortmund 1-3 Wolfsburg - LOST
Klopp's last season in charge of Borussia Dortmund, in which they slumped to a seventh-placed finish in the Bundesliga, ended with another German Cup final defeat - this time to Wolfsburg.
Dortmund made a perfect start, with Pierre-Emerick Aubameyang giving them the lead just five minutes in, but Wolfsburg produced an emphatic response, scoring three goals in 16 first-half minutes. Luis Gustavo got the first, with Kevin De Bruyne and Bas Dost putting another trophy out of Klopp's reach.
2016 Capital One Cup - Liverpool 1-1 Man City - LOST ON PENALTIES
Klopp had his first opportunity to lift silverware at Liverpool just four months after his appointment as they reached the League Cup final against Manchester City. They were many people's favourites having thrashed Manuel Pellegrini's side 4-1 at the Etihad Stadium in November, but City were far stronger at Wembley.
Philippe Coutinho sent the tie to extra-time when he cancelled out Fernandinho's opener, but Liverpool's goalscorer was one of three Reds players to miss their penalties as City won the shootout 3-1.
2016 Europa League - Liverpool 1-3 Sevilla - LOST
Liverpool overcame Manchester United and Borussia Dortmund on their way to the 2016 Europa League final and they appeared to be on their way to lifting the trophy when Daniel Sturridge opened the scoring against Sevilla with a stunning strike at the St Jakob-Park stadium in Basel.
But having gone into the break with a one-goal lead, Liverpool suffered a depressing second-half collapse. Kevin Gameiro equalised in the first 17 seconds, with Coke scoring twice in the space of six minutes later in the half. "I am responsible for this performance," said Klopp afterwards. "I promise everybody we will use it and come back stronger."
2018 Champions League - Liverpool 1-3 Real Madrid - LOST
Gareth Bale scored one of the best goals in Champions League history as Real Madrid retained their title. Karim Benzema capitalised on Reds goalkeeper Loris Karius' error to put Real ahead in the 51st minute before Sadio Mane levelled four minutes later.
Bale then stunned Klopp's side with a stunning overhead bicycle kick in the 64th minute, before another blunder from Karius saw the Wales striker add the third for Real in the 83rd minute.