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Jurgen Klopp will wave farewell to Anfield on Sunday after nine glorious years at Liverpool, having marshalled the club to Premier League, Champions League and domestic cup honours. 

The German will undoubtedly go down as one of the greatest Liverpool managers of all time, with Mail Sport’s Ian Ladyman claiming on Thursday that Klopp’s 2021-22 team was better than any forged under Bob Paisley or Bill Shankly.

He brought the title back to Anfield in 2020 after a dismal 30-year drought and had the quadruple in his sights in 2022, before Manchester City won the Premier League by a point and Real Madrid triumphed in the Champions League final.

Mail Sport takes a look at the biggest flops to represent Klopp during his reign.  

Jurgen Klopp will wave farewell to Anfield on Sunday after nine glorious years at Liverpool

Jurgen Klopp will wave farewell to Anfield on Sunday after nine glorious years at Liverpool

The German has lured a hatful of trophies to Liverpool and forged a series of brilliant teams

The German has lured a hatful of trophies to Liverpool and forged a series of brilliant teams

But not every player has been a success. Mail Sport looks at some of the flops from his reign

But not every player has been a success. Mail Sport looks at some of the flops from his reign

ADAM BOGDAN

(Free from Bolton Wanderers, 2015)

Adam Bogdan was given his first Premier League start by Klopp but things quickly went downhill. 

Three minutes into a game against newly-promoted Watford, a corner was floated to Bogdan under no pressure, which he spilled for Nathan Ake to finish. Only two weeks later against Exeter City, he made the exact same mistake.

Reds fans were forced to nail bite at every corner they faced from that moment on, with the Hungarian remaining at the club until his move to Hibernian in 2019.

Adam Bogdan made a hatful of errors after winning his Liverpool chance and didn't recover

Adam Bogdan made a hatful of errors after winning his Liverpool chance and didn’t recover

CONNOR RANDALL

(From Liverpool’s Academy, 2015)

Coming through the youth ranks from the age of eight, Connor Randall was given his big break by Klopp. 

However, the German soon shunted the boyhood Red after he failed to make an impact and turned to emerging youngster Trent Alexander-Arnold – which proved the right decision. 

Randall was substituted after Liverpool went 2-0 down at half-time against Wolves in the FA Cup and was never seen again in Red. Not long after, he joined Bulgarian club Arda Kardzhali.

Connor Randall was given his break by Klopp after emerging through the club's youth ranks

Connor Randall was given his break by Klopp after emerging through the club’s youth ranks

TIAGO ILORI

(£7m from Sporting, 2012)

When the highly-rated Tiago Ilori made his move to Merseyside in 2012, the FA were hoping to persuade the London-born defender to play for England rather than Portugal following his exit from Lisbon-based Sporting. 

But the £7million man was hardly used at Liverpool before going out on two loan spells. When Klopp took over, the German admitted he had no idea that Ilori played for his team. 

Proving a poor investment, Ilori made just three appearances under Klopp before moving to Reading in 2017.

Tiago Ilori, pictured in action for Portugal's youth team, joined Liverpool back in 2012 and made just three appearances for the Reds under Klopp before moving to Reading in 2017

Tiago Ilori, pictured in action for Portugal’s youth team, joined Liverpool back in 2012 and made just three appearances for the Reds under Klopp before moving to Reading in 2017

OZAN KABAK

(£1m loan from Schalke, 2021)

With Klopp’s side facing a centre-back injury crisis at the time, Ozan Kabak was brought in on a £1m loan deal from Schalke. But he ultimately failed to solve the German’s problems. 

The Turkish international made a terrible first impression on his debut, losing 3-1 at the King Power to Leicester. 

Liverpool declined Kabak’s £18m buy option after he failed to impress across his nine appearances for the club.

Ozan Kabak was brought in on a £1m loan deal from Schalke to save Klopp from an injury crisis

Ozan Kabak was brought in on a £1m loan deal from Schalke to save Klopp from an injury crisis

BRAD SMITH

(From Liverpool’s Academy, 2013)

Brad Smith came all the way from Australia to play youth football for the Reds after being scouted at his local high school team. 

In just his second appearance, Smith was sent off after being booked following two clumsy challenges as his side were beaten 3-1 at the Liberty Stadium by Swansea.

The Australian featured only three times more for Liverpool before joining Bournemouth for £6m.

Ex-Reds left-back Brad Smith (foreground) pictured with the Liverpool manager back in 2016

Ex-Reds left-back Brad Smith (foreground) pictured with the Liverpool manager back in 2016

KEVIN STEWART

(Free from Tottenham Hotspur, 2014)

Once hailed as the next Xabi Alonso, Kevin Stewart joined the Reds from Tottenham on a free. 

Klopp described the former Jamaica international as the best tackler at the club, but he only made nine appearances after detrimental injuries. 

He clearly failed to live up to his high margins set which resulted with a move to Hull City in 2017.

Kevin Stewart joined the Reds from Tottenham on a free before enduring a litany of injuries

Kevin Stewart joined the Reds from Tottenham on a free before enduring a litany of injuries

MARKO GRUJIC

(£5.1m from Red Star Belgrade, 2016)

Marko Grujic was once one of Europe’s most wanted young players with Juventus, Chelsea, and AC Milan all interested in the Serbian – but it was Klopp who won the race after personally calling the defensive midfielder to join Anfield.

The German’s first ever Liverpool signing was dubbed the ‘Serbian Steven Gerrard’ but played just 16 times for Liverpool, scoring once.

Grujic took aim at Klopp, blaming his lack of development on the manager’s decision to sign big-money midfielder Thiago. He later joined Porto on a season-long loan and made the move permanent a year later for £10.5m.

Marko Grujic was Klopp's first ever Liverpool signing and dubbed the ‘Serbian Steven Gerrard’

Marko Grujic was Klopp’s first ever Liverpool signing and dubbed the ‘Serbian Steven Gerrard’

ARTHUR MELO

(£4m loan from Juventus, 2022)

Arguably Klopp’s biggest flop, Arthur Melo came from Juventus on loan to provide desperate cover in the Reds’ understaffed midfield. 

Expected to play a vital role in Klopp’s bid for glory after impressing at Barcelona and Juventus, he could not have been any further from what the Reds needed. 

The former Brazil international played just 13 minutes for Liverpool, coming off the bench in the Champions League against Napoli before suffering a long-term thigh injury. 

Liverpool chose not to buy Arthur for £32.5m at the end of one of the worst loan spells of all time.

Arthur Melo's move to Liverpool will go down as one of the worst loan deals in football history

Arthur Melo’s move to Liverpool will go down as one of the worst loan deals in football history

JORDON IBE

(£750,000 from Wycombe Wanderers, 2012)

Jordon Ibe was supposed to be one of the best up-and-coming English wingers, having become the youngest ever Football League player at just 15 with Wycombe, where Liverpool snatched him up. 

Expected to fill the boots of the departed Raheem Sterling, the prospect proved to big for the youngster, who had issues off the pitch and scored just once for the Reds in 41 games. 

Ibe joined Bournemouth in 2016 for £15m – which had Reds fans laughing at the fee.

Jordon Ibe joined Bournemouth in 2016 for £15million despite proving a flop for Liverpool

Jordon Ibe joined Bournemouth in 2016 for £15million despite proving a flop for Liverpool

RHIAN BREWSTER

(£250,000 From Chelsea’s Academy, 2015)

One of the first talents Klopp spotted, Rhian Brewster failed to reach his potential after joining Liverpool’s academy from Cobham. 

Despite a hatful of goals in his youth, he never managed to score for the Reds – having never made a Premier League appearance for Liverpool. 

He did, however, feature on Klopp’s bench during the 2019 Champions League final and collected a winner’s medal. 

In 2020, he moved to Sheffield United for £23.5m, flopping even worse for the Blades.

Rhian Brewster failed to reach his potential after joining Liverpool’s academy from Cobham

Rhian Brewster failed to reach his potential after joining Liverpool’s academy from Cobham

JOAO CARLOS TEIXEIRA

(£830,000 From Sporting’s Academy, 2012)

Joao Carlos Teixeira once drew comparisons with Deco, having impressed within Sporting’s youth ranks. 

Klopp gave the Portuguese playmaker his first appearance against Fulham in 2014 during their title push. 

Liverpool flop Joao Carlos Teixeira (left) jostles for the ball against West Ham's Winston Reid

Liverpool flop Joao Carlos Teixeira (left) jostles for the ball against West Ham’s Winston Reid

These are the top flops of the Klopp era, as determined by Mail Sport in a loose 4-3-3 formation

These are the top flops of the Klopp era, as determined by Mail Sport in a loose 4-3-3 formation

He pulled off a vital block in the dying minutes of Liverpool’s 3-2 win and later revealed that skipper Gerrard said: ‘That, what you did there, was f****ing brilliant!’.

Unfortunately, that was as good as it got for Teixeira. He made just seven more appearances for Liverpool before moving back to his homeland in Porto.

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