During that time Klopp has cemented himself as one of the sport's all-time greats in terms of triumphs, counting Liverpool's first (and long coveted) Premier League crown and a Champions League trophy amongst his many accolades.
But the towering German has also proved himself to be one of English football's greatest-ever characters, providing a stacked highlight reel of entertaining moments on and off the pitch.
Here, Flashscore takes a quick look at some of Klopp's greatest hits away from his football success during his revered time at Liverpool's helm.
Laughing at Lucas Leiva
In Klopp's first season with the Reds, he began getting a taste for camera-friendly antics that he would soon become synonymous with.
During a Merseyside Derby encounter against Everton in 2016 - during which Liverpool were cruising to a 4-0 victory - Brazilian midfielder Lucas Leiva picked up the ball on the outskirts of the opposition box two minutes into added time.
Never renowned for his goalscoring prowess (he scored just one league goal in 10 years with Liverpool), the Anfield crowd urged Leiva to take a shot, which he duly did.
However, the ball trickled at something resembling a snail's pace harmlessly wide, much to the amusement of Klopp in the dugout, who is swiftly caught on camera giggling away with his assistants.
He probably would've reacted differently with the scores still level, but Klopp saw the funny side.
"We enjoyed the situation when Adam, Alberto, and Phil had a little bit of fun on the sideline and gave the ball to Lucas, who destroyed this wonderful moment," Klopp said afterwards.
A champion's rap
Lifting the Champions League trophy for the sixth time in the club's history - and his first - is an accomplishment worthy of a victory lap. For Klopp, that victory lap came with a unique twist – an on-air serenade that surprised both journalists and fans alike.
The final whistle blew, and the usual post-match intensity melted away. In its place, stood a relieved and joyful Klopp, a man basking in the warm glow of a hard-fought victory over Tottenham in Madrid back in 2019.
His normally focused demeanor morphed into one of pure enjoyment, as he readily chatted with journalists, the celebratory champagne still buzzing in his veins.
Suddenly, he took a playful turn. Ditching the usual tactical analysis, Klopp playfully grabbed the microphone and, with a mischievous grin, began to sing.
"Let's talk about six baby, let's talk about you and me," Klopp crooned, his gaze flitting between the journalist and the coveted trophy, "let's talk about all the good things, and all the bad things that may be, let's talk about six!"
"That's a new song," the manager then said straight to the camera with a grin.
Pep Guardiola is coming!
A playful exchange unfolded at the UEFA Elite Club Coaches Forum in Nyon, Switzerland, as Liverpool manager Jurgen Klopp sidestepped a potentially awkward interview moment with a wink towards the approaching Pep Guardiola back in 2019.
When asked by a reporter if he'd spoken with "Pepe," a momentarily confused Klopp feigned ignorance: "Pepe? Who is Pepe?"
The reporter clarified, trying to lighten the mood: "Pepe (with slightly less emphasis on the second e) Guardiola."
With their well-known rivalry now probably at its highest peak on the pitch, Klopp playfully shouted: "Pep!"
"Not Pepe, Pep," the reporter corrected, this time omitting the second e altogether.
Chuckling, Klopp acknowledged the game: "It's not Pepe in Italy, okay, okay."
Finally, the reporter conceded with a smile: "It's Pep."
Klopp, seemingly satisfied with the playful back-and-forth, gathered himself and answered sincerely: "Yes of course we spoke. Why shouldn't we speak? We speak constantly."
But as if on cue, the source of all the merriment entered the room – Pep Guardiola himself. With a mischievous glint in his eye, Klopp lowered his voice and whispered to the camera: "Pep Guardiola is coming," before turning and making a hilariously hasty retreat, leaving the reporter and surrounding onlookers in stitches.
Brain f***
Post-match football interviews are done a little differently over in Germany, where managers and players aren't restricted by a TV watchdog and are free to speak their minds using whatever colourful language they wish.
Not so much in the UK though, where swearing is still seen as a naughty thing to do through official channels.
Klopp's been caught out a bit by this before, but none of those moments were quite as funny as his mishearing of the word "brain fog" during a press conference in 2022.
The coach was speaking to reporters ahead of Liverpool’s Premier League game against Newcastle when he had a question of his own in response to one reporter, who had used the term.
"Why can everyone say the word and then if I say it, it's not okay?", Klopp queried.
When asked what he meant, Klopp replied: "Brain f***."
The journalists in the room then burst into laughter while Klopp simply looked perplexed.
"Oh, so you didn’t say that - what did you say?", he asked.
A member of the press then replied: "Fog. F. O. G.", before explaining its meaning.
Klopp then replied: "Oh, okay. It sounds to my ears exactly the same to be honest!"
This probably means Klopp had been assuming everyone was swearing whenever he heard the word "fog."
Pulled hamstring
One of the most amusing moments in recent memory came in the 2022/23 season when an angry dressing down of the fourth official during a game against Tottenham was cut short by a pulled hamstring.
He had been back-and-forth with the officials all afternoon - something he would later be criticised for - and after a topsy-turvy match in which Spurs came back from 3-0 down to level in added time, he jubilantly celebrated in the face of the fourth official when Diogo Jota had won it for his side.
En route though, Klopp appeared to pull his hamstring and limped away from the exchange.
Klopp said after the game: "I'm not sure it’s a hamstring. It could be an adductor as well. It's painful."
He was still putting himself about on the pitch at full-time, mind.
One ring to rule them all
Anfield erupted in joyful chaos after Liverpool's nail-biting victory over Newcastle on New Year's Day.
Klopp, ever the maestro of the post-match celebrations, led the roaring Kop in a raucous chorus of 'You'll Never Walk Alone.' But amid the frenzy, a flicker of worry crossed his face as he abruptly broke off, eyes darting down to the turf.
The Sky Sports cameraman, trained on Klopp's every move, captured the brief moment of concern.
Had the weight of the win finally caught up to him? No, within seconds, the reason became clear. Klopp wasn't lost in thought - he was lost in panic.
His wedding band had slipped off his finger and vanished somewhere amongst the ecstatic throng. Relief washed over the jubilant crowd as, minutes later, Klopp reappeared, beaming ear to ear, the ring safely back on his finger.
In a post-match interview, Klopp declared the Sky Sports cameraman his "new hero for 2024."
"I lost it once in my life and needed a professional diver because I lost it in the sea," Klopp said afterwards.
"I'm not into jewellery," he chuckled, "but this is the one ring I can't live without!
"The cameraman annoyed me quite a lot of times already this season but today he has a lot of shots for you.
"If he wants my full face in the camera, then he can have it."