Staying up, pain, glory - Ten games that made Klopp as Liverpool boss hits 1,000

Over 999 matches as a manager Jurgen Klopp really has seen it all.

From Mainz to Borussia Dortmund to Liverpool, Klopp has experienced everything that the game has to throw at you, from glorious victories, league titles, promotions and cup wins to relegation, final defeats and heartbreak.

It has been an eventful career, and as he prepares for his 1,000th match as a manager when Chelsea come to Anfield on Saturday he is sure to be reminiscing about the highs and lows.

But what are the matches that have made Klopp?

We've taken a look back at 10 of his most important games across a storied career.

1. The first: Mainz 1-0 MSV Duisburg - February 28, 2001

We start at the beginning.

Klopp, then 33, was cast into the role of Mainz manager just a matter of weeks after his retirement as a player in early 2001.

A rough and ready defender/striker who played 346 games for the club, Klopp was asked to save them from what would have been a disastrous drop into the German third tier.

He oversaw a 1-0 win over Duisburg in his first game in charge, and that kicked off a run of six wins in his first seven games in charge.

Mainz would end up staying in the 2. Bundesliga by a point, and their young manager had started out on a journey.

2. Third time lucky: Mainz 3-0 Eintracht Trier - May 23, 2004

Taking inspiration from his former Mainz boss Wolfgang Frank, a key figure in his career, Klopp was able to take his side from relegation candidates to vying for a place in the Bundesliga.

They finished fourth in both of his first two full seasons, just outside the automatic promotion places, before a 3-0 win over Eintracht Trier on the final day of 2003-04 earned them an historic third place to take them up on goal difference.

It is an experience Klopp has never forgotten, with the two near misses also serving him well when reacting to setbacks throughout his career.

"I can promise we had a beautiful evening," former club president Harald Strutz told the BBC in 2020.

"Jurgen always tells me he has this image of me that he'll never forget. Standing in a pub at 3 o'clock in the morning looking so happy. Smiling, laughing, drinking."

3. Laying down a marker: Borussia Dortmund 2-0 Bayern Munich - October 3, 2010

After establishing Mainz in the Bundesliga despite having the smallest budget, Klopp's side were relegated in 2006-07 before bouncing straight back up. That was, the manager felt, a good position to leave them in, and he left for Borussia Dortmund in 2008.

Encouraging signs were seen in his first two seasons, but it wasn't until early in the third that things looked like they were really beginning to click.

Goals from Lucas Barrios and Nuri Sahin gave Klopp's Dortmund a 2-0 win over Louis van Gaal's struggling Bayern Munich in early October, the middle of a run of 14 straight victories.

It was also the first of five straight wins for Klopp's side over Bayern, and set them en route to the title, which was secured by seven points at the end of the season.

4. Mauling Mourinho: Borussia Dortmund 4-1 Real Madrid - April 24, 2013

Back-to-back Bundesliga titles had established Klopp's Dortmund as one of the best sides in Europe, and they were turning heads in the Champions League too.

Yet when Jose Mourinho's Real Madrid came to town in the semi-finals many expected the Spanish giants' greater nous and their manager's greater reputation to win out. Klopp's side were having none of it.

Robert Lewandowski scored four goals in a dominant 4-1 win, but after protecting that lead in the second leg and reaching the final, Klopp's side would lose out to old rivals Bayern Munich at Wembley.

With players leaving for riches elsewhere, things were never quite the same for him at Dortmund again.

5. That's what he can do: Manchester City 1-4 Liverpool - November 21, 2015

After leaving Dortmund in the wake of a tumultuous season in 2014-15, Klopp took a brief break before being dropped into a Liverpool that had lost its way in the final throes of Brendan Rodgers' tenure.

There was quickly a sense that if this charismatic German couldn't guide Liverpool to success then perhaps no-one could, and early indications of just what he could be capable of saw the Reds win 3-1 away at Chelsea, who had Mourinho, and then 4-1 at Manchester City.

Previously underperforming and unconvincing players - including Roberto Firmino, who scored his first goal for the Reds that day at the Etihad - suddenly looked reborn, and there was a sense that this could be special.

6. "No-one leaves here before 1am": Watford 3-0 Liverpool - December 20, 2015

For every up in those early days though, a down wasn't too far away.

Liverpool were still hugely inconsistent, and a month after that win at City came a meek surrender at Watford on the day of the club's Christmas party.

Most bosses would have cancelled the bash in the wake of such a result, but Klopp insisted it went ahead as he wanted his side to win and lose as a team, eventually telling his players: "Right now, this is our priority. I don't mind whether you drink, but no-one leaves here before 1am."

They were the manager's orders, and his authority wasn't questioned.

7. Among the elite: Liverpool 3-0 Middlesbrough - May 21, 2017

In the late 2000s Liverpool forged a reputation as one of the Champions League's most consistent teams, but after dropping off in the final days of Rafa Benitez they had played in it just once in seven years - and that a meek attempt under Rodgers in 2014-15.

Klopp knew he needed to get the Reds back into the competition to kick start the work he really wanted to do, and he got there on the final day of his first full season with a 3-0 win over Middlesbrough at Anfield which was kickstarted by a fine Gini Wijnaldum goal on the stroke of half-time.

Liverpool weren't just back in the big time, they were there under this manager, and those two elements combined would produce quite a reaction.

8. The start of something: Real Madrid 3-1 Liverpool - May 26, 2018

And Liverpool didn't just qualify for the Champions League, they made it all the way to the final.

A thrilling Reds side played some superb football en route to facing Real Madrid in Kyiv, but it was there that their dream would come crashing down in a cruel fashion, with those errors from Loris Karius and that stunning Gareth Bale goal giving Real victory.

No matter.

A new bond had been forged between Liverpool's manager, players and fans on the way to that final, and there was a belief that a place at the elite of the game could be grasped by a side that longed to be there.

Things were about to go into overdrive.

9. "Because it's you, we have a chance": Liverpool 4-0 Barcelona - May 7, 2019

After engaging in a remarkable, punch for punch Premier League title race against Manchester City, Liverpool were staring at the possibility of ending the season empty handed.

A harsh 3-0 defeat in the first leg of their Champions League semi-final had meant that route to glory seemed over, and when Vincent Kompany's bolt from the blue gave City a 1-0 Premier League win over Leicester the following week, the season looked over.

Twenty-four hours later, and without the injured Firmino and Mo Salah, Liverpool produced perhaps the greatest European comeback of all time to win 4-3 on aggregate and reach the Madrid final, where they would beat Tottenham a lot more conventionally.

In the team's hotel on the afternoon of the Anfield semi, Klopp had drilled home a message to his team.

"Mostly, I talked about tactics. But I also told them the truth," he would later write in The Players' Tribune.

"I said, 'We have to play without two of the best strikers in the world. The world outside is saying it is not possible. And let's be honest, it's probably impossible. But because it's you? Because it's you, we have a chance.'

'I really believed that. It wasn't about their technical ability as footballers. It was about who they were as human beings and everything they had overcome in life.

'The only thing that I added was, 'If we fail, then let's fail in the most beautiful way.'"

10. The sign of champions: Aston Villa 1-2 Liverpool - November 2, 2019

After the Champions League was secured thoughts would immediately turn to the Premier League, and towards ending Liverpool interminable wait for the title.

Klopp's time at Anfield would, after all, be judged as a failure if he didn't win it, and after a lightning quick start to the 2019-20 campaign there really was no stopping them.

Late, gutsy wins were becoming the norm, and none was later or more gutsy that a 2-1 success at Aston Villa achieved courtesy of an 87th minute Andy Robertson equaliser and Sadio Mane's 94th minute winner.

Liverpool went six points clear, a lead which few to nine the following week when they beat Manchester City.

There was no catching them.