Klopp was still seeking his first win as Reds boss when he first encountered the competition in October 2015.
Nathaniel Clyne's debut goal for the club was enough to beat Bournemouth and for the German to secure his first victory, his tenure up and running.
And the League Cup went on to form an important part of the first 18 months of Klopp's reign as he began transforming the team towards his intended vision.
Jurgen Klopp, manager looks dejected in defeat after the Capital One Cup Final match between Liverpool and Manchester City at Wembley Stadium (Image: Clive Brunskill/Getty Images)
That first season, as Rafael Benitez had during his debut campaign in charge at Anfield, the Reds boss guided Liverpool to the final, only to be beaten on penalties by Manchester City.
The following campaign, the semi-final was reached before defeats home and away to Southampton in the semi-final put paid to a Wembley return.
Last year's stumble at the first hurdle, losing 2-0 to Leicester City in the third round, underlined the difficulty of negotiating a competition that has in effect become a barometer of a club's squad strength.
Leading Premier League teams, at least until the closing stages of the competition, are minded to field a mixture of regulars, fringe players and youngsters.
Liverpool manager Jurgen Klopp bends over backwards in frustration on the sidelines during his side's fixture against Bournemouth in the Capital One Cup at Anfield. Photo by James Maloney
Klopp is no different, although he had to learn quickly about the unique demands of what is still regarded the lesser of the major trophies on offer each season.
“There are a lot of things when you come to a new country and you have no clue about it,” he says. “One of the things I had was people judging cup competitions before I played them.
“My first cup game was Bournemouth. Everyone was telling me that I needed to play the kids or whatever. I thought 'I can play the kids but I can’t play all of them'. It was never like this.”
That said, consider Liverpool's starting line-up in that tie against Bournemouth: Adam Bogdan in goal, Connor Randall in defence, Cameron Brannagan, Jordon Ibe and Joao Teixeira in midfield.
Jurgen Klopp manager of Liverpool reacts before the Capital One Cup Fourth Round match between Liverpool and AFC Bournemouth at Anfield on October 28, 2015 in Liverpool, England. (Photo by John Powell/Liverpool FC via Getty Images)
It's a world away from the team Klopp will field against Chelsea at Anfied on Wednesday in the third round's most eye-catching tie, even if the Reds boss makes, as is expected, a raft of changes.
“There are plenty of games,” he says. “We judge the situation, not the competition. We think 'how will the opponent line up?' and stuff like this.
“There is always something that we have in our mind. It is never the competition. We never say 'oh, it’s the League Cup'. The final is in February, it’s Wembley.
“When we were there the last time, we really wanted to win it. We were close but we didn’t. That’s how it is.
“We will try again. But it’s not about judging the silverware. You cannot do it like that.”
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Carabao Cup preview Liverpool v Chelsea
Klopp is still awaiting his first silverware as Reds boss, and the League Cup offers value in being the first major trophy any team can win each season.
Other managers have viewed the competition accordingly. Joe Fagan's first trophy as Liverpool boss was the League Cup, so too Roy Evans, Gerard Houllier and, most recently, Kenny Dalglish during his second stint in charge.
Elsewhere, it was the first trophy won by Jose Mourinho in each of his stints as Chelsea manager and his current time at Manchester United, while George Graham's glory days at Arsenal began with a League Cup final win over Liverpool in 1987, similar to Brian Clough's at Nottingham Forest in 1978. And Manuel Pellegrini's first silverware while Manchester City boss came in the competition in 2014.
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