As August looms, Liverpool’s transfer window remains delicately balanced, with deals for Mohamed Salah, Dominic Solanke and Andrew Robertson done, but Jürgen Klopp’s continued pursuit of Southampton’s Virgil van Dijk and RB Leipzig’s Naby Keïta remains extremely problematic.

Liverpool are no strangers to experiencing frustration with transfer targets – numerous players have come close to joining the Reds, only to choose another club, or to see their current club pull out of any deal, or even fail medicals and personal terms.

Liverpool have witnessed these unfortunate situations throughout their history, but in particular during recent years under the club’s current owners, Fenway Sports Group.

The Reds may have been prudent with their finances under FSG, shaped by poor transfer deals early on in their stewardship, their ‘Moneyball’ strategy and the mess surrounding the summer of 2014, amongst other factors.

In fairness, FSG do appear to be firmly behind their main man in Klopp, submitting huge transfer bids for Keïta according to reports and being prepared to make van Dijk the world’s most expensive defender. Yet while those deals remain uncompleted, Keïta and van Dijk could join a lengthy list of players Liverpool have missed out on since the new owners took over in 2010.

Here is only a sample containing some of the more famous examples:

Diego Costa

In the summer of 2013, Liverpool submitted a bid of over £20m for Diego Costa, then at Atletico Madrid. It was unclear whether Costa would be a replacement for Luis Suárez, who at the time was looking to leave Anfield for Arsenal, or as a compliment to the Uruguayan and Daniel Sturridge.

Yet Costa turned down Brendan Rodgers to remain in Spain, before leading Atletico to La Liga glory in 2014 alongside the Champions League final, before his move to Chelsea a year after rejecting Liverpool.

Yevhen Konoplyanka

Same season, only this time at the end of the January transfer window. Rodgers wanted extra quality to sustain Liverpool’s surprise title challenge, and looked towards Konoplyanka, then at Ukrainian side Dnipro.

Liverpool appeared to match Konoplyanka’s buyout clause of over £15m, however the Dnipro president, Ihor Kolomoyskyi, would not release Konoplyanka, despite the deal progressing to the extent that Liverpool had arranged a medical in Ukraine.

Konoplyanka remained at Dnipro, joined Sevilla on a free transfer in 2015 and enjoyed mixed success in Spain and also since with German side FC Schalke. Meanwhile, everyone sadly knows how Liverpool’s 2013/14 season ended – and we will never know whether Konoplyanka would have made any difference to the final outcome.

Willian

A trio of Premier League clubs were involved in the scramble for Brazilian sensation Willian in 2013. After six months in Russia with Anzhi Makhachkala, the club abruptly lost its investment and had to transfer list the entire squad, attracting the interests of Liverpool, Tottenham Hotspur and Chelsea.

Liverpool were first, hoping to land a marquee attacker following the failure to sign Costa and Henrikh Mkhitaryan. Yet, in what has since become a common theme, Willian preferred a move to London, which placed Tottenham in pole position before Chelsea snatched the player in a £30m deal, and he has become an important and consistent figure in the squad at Stamford Bridge.

Clint Dempsey

A year prior, in Rodgers’ first summer window at Liverpool, the club attempted to seal a very late deal for Fulham’s American star Clint Dempsey to replace West Ham-bound Andy Carroll.

However, the deal turned sour, with Fulham eventually accusing the Reds of tapping up Dempsey, and Liverpool issued an apology in December 2012, in a similar vein to the van Dijk statement over a month ago.

Ultimately, Dempsey moved to Tottenham on the final day of the August 2012 transfer window, during a period where it appeared the North London club had first refusal on Liverpool targets, including Willian, Christian Eriksen and Gylfi Sigurdsson (see below).

Liverpool’s failure to sign Dempsey was not all bad though – the club held onto future captain Jordan Henderson, who was offered to Fulham as part of the Dempsey deal, and would later sign Daniel Sturridge in January to partner Suárez.

Gylfi Sigurdsson

Now embroiled in a transfer saga with Merseyside rivals Everton, Gylfi Sigurdsson five years ago had the choice of moving from Hoffenheim to either Tottenham or Liverpool, after a successful loan spell at Swansea City.

Liverpool appeared favourites – after all, Rodgers had launched Sigurdsson’s Premier League career at Swansea and the Icelandic midfielder was all set for a permanent move to South Wales before Rodgers left for Liverpool.

The Northern Irishman offered Sigurdsson the chance to follow him to Anfield, but he chose to sign for Tottenham instead, citing a greater chance of playing in the Champions League at White Hart Lane, although finances may have been another factor. Sigurdsson is now back at Swansea, although perhaps for not too much longer.

Loïc Rémy

This deal was all but done. Liverpool had activated Rémy’s release clause from Queens Park Rangers and the Frenchman appeared an exciting signing in Liverpool’s 2014 rebuild, having impressed on loan for Newcastle United.

However Liverpool pulled out of the transfer after Rémy failed his medical, fearing heart problems. The Frenchman subsequently joined Chelsea with no issues and won the Premier League and League Cup in his debut season.

Dele Alli

One Liverpool may regret for a long time. Dele Alli, a Liverpool and Steven Gerrard fan, appeared set for a move to his boyhood club after greatly impressing with MK Dons. Negotiations took place to bring Alli to Anfield in 2014, with Rodgers personally involved, but ultimately Liverpool’s transfer committee did not believe Alli was worth the excessive finances for a player of his age.

Alli later joined Tottenham in January 2015 for around £5m, and has since made that fee a bargain. He is already one of England’s best players at 21 and is a cornerstone of Tottenham’s recent success. Possible Steven Gerrard successor? Liverpool will hope not.

They will also hope history does not repeat itself with Fulham’s Ryan Sessegnon, after the 17-year-old turned down Klopp to remain in London this summer.

Mario Götze

The German wünderkid who scored the winning goal for Germany in the 2014 World Cup final had lost his way at Bayern Munich, but appeared set for a reunion with his former Borussia Dortmund boss Klopp last season. Bayern were keen to sell, with a fee of around £20-25m mooted, and Liverpool fans were excited at the thought of a world-class talent arriving at Anfield.

Yet Gӧtze’s real interest in Liverpool appeared to be their potential Champions League football on offer, as once the Reds lost the Europa League final to Sevilla in 2016, he joined his old club Dortmund instead of joining his old boss at Liverpool. However, he has badly struggled in his return with injuries and fitness issues and is not loved by the Dortmund fans, who remember his Bayern past.

Liverpool meanwhile brought in Sadio Mané from Southampton, and all can agree that the Senegalese has been a rather successful alternative to Gӧtze, to put it mildly. Therefore, one positive of that Europa League defeat was landing Mané over Gӧtze, who played a vital role in securing Champions League for this season.

Alexis Sánchez

Arguably Liverpool’s biggest missed target under FSG. Alexis Sánchez should have been included in Liverpool’s deal to sell Suárez to Barcelona, but unfortunately Liverpool took £75m in cash instead and pursued Sanchez separately. Arsenal entered the chase and Sánchez preferred to live in London and work with Mesut Ӧzil and Arsène Wenger, leaving Liverpool frustrated and without an adequate replacement for Suárez.

Ultimately, Rickie Lambert and Mario Balotelli led the line for Liverpool in the 2014/15 season, emphasising the extent of Liverpool’s failure to land Sánchez in 2014, and the Chilean has elevated himself at Arsenal, becoming one of the very best players in the world.

Mohamed Salah

Finally, Liverpool may now have Mohamed Salah on their books, but it appeared for a while that the Egyptian would be another player who had slipped away.

Chelsea signed Salah in January 2014 from Swiss club Basel after Liverpool had failed to meet Basel’s valuation for the winger. Yet the 25-year-old was barely given a chance at Stamford Bridge, and went out on loan to Fiorentina and Roma, signing for the latter on a permanent deal.

After starring in the Italian capital, Liverpool, now under Klopp, tried a second, and successful, attempt for Salah, and will hope to wrap up deals for Keïta and van Dijk next month, so that the Reds do not regret on missing out on more prized targets.