#3 2015–16 UEFA Europa League
Liverpool suffered another heartbreak the same season they lost to Manchester City in the league cup final, but this time, it was on the European front.
Jurgen Klopp masterminded wins over Manchester United and former employers Borussia Dortmund in the round of 16 and quarter finals respectively, before beating Villareal in the semi-final 3-1 on aggregate, setting up a final clash against current Arsenal manager Unai Emery who was the coach of Sevilla.
Expectations were high. In the first half, Liverpool raced to a one-nil lead courtesy of a Daniel Sturridge strike. However, in the second half, Sevilla fought back and scored early in the second half through Kevin Gameiro and a brace from Coke to defeat The Reds 3-1.
#4 2017–18 UEFA Champions League
This was perhaps the most disappointing of all defeats in cup finals of Jurgen Klopp's managerial career. Liverpool was particularly impressive. One of the most remarkable wins was the convincing 5-1 aggregate win over English champions Manchester City.
But again and again, they bowed to pressure and conceded two goals scored by Gareth Bale.
All of these failings bring to the spotlight Jurgen Klopp's inability to rouse his team for the occasion when it matters most.
This season, Liverpool have lost a hope of winning another League Cup trophy. They lost out to Chelsea at Anfield in the Carabao cup third round tie.
They also face being eliminated from the UEFA champions league after losing 2-0 to Red Star Belgrade. They face difficult fixtures away at Paris Saint Germain and a home game versus Napoli.
The Premier League is a very tight contest as things stand and Liverpool cannot claim to be the overwhelming favourites for the title.
The English FA cup also known as the Emirates FA cup presents the only tangible opportunity for Klopp to break the jinx. It would be difficult because of its giant-killing reputation.
It also comes at a period when Liverpool will probably want to concentrate on the English Premier League title chase. Only time will tell if Klopp will break this long standing jinx.