Kevin Keegan (Hamburg, 1977)

This was the 1970s, agents were a rarity, transfer windows didn’t exist, yet on Merseyside there was a man with a release clause. Yes, as well as appearing in Brut adverts, ‘KK’ was plotting his future in a manner that was ahead of his time, insisting Liverpool put a £500,000 clause in his contract so as to open up the possibility of a lucrative move abroad. And that is just what Keegan secured in 1976 – just like the Beatles he was heading to Hamburg.

The Kop was in shock and anguish. Their first modern-day superstar, a whirlwind of determination and ruthlessness who had helped Liverpool to two league titles, two Uefa Cups and an FA Cup having arrived from Scunthorpe five years earlier, was off. This type of thing simply didn’t happen at Anfield.

There was still an entire season for Keegan to play before he departed for Germany and it was a tense one for the striker, with Liverpool fans openly questioning his loyalty. But yet again Keegan simply got on with the task of harassing defenders and scoring lots of goals. In the process he also helped Liverpool win their 10th league title and first European Cup on a balmy night in Rome.

What happened next? Bob Paisley signed Kenny Dalglish from Celtic for £440,000 and handed him Keegan’s No7 shirt. In return the Scot scored the winning goal in the 1978 European Cup final and went on to become the greatest player in Liverpool’s history. So not a bad replacement, then. Over in Germany, Keegan also made quite an impression, helping Hamburg to the 1979 Bundesliga title and himself to a couple of European Footballer of the Year awards.

Graeme Souness (Sampdoria, 1984)

Graeme Souness’s final act as a Liverpool player was to lift the 1984 European Cup. He then joined Sampdoria for £650,000. Photograph: Allsport/Getty Images

Rome 1984, and Liverpool win their fourth European Cup. They’re back at the Stadio Olimpico where it all started seven years previously and having beaten Roma on their own turf the men in red are naturally elated, no one more so than the captain. Yet as Graeme Souness lifts ‘Old Big Ears’ into the night sky, he knows it will be his last act as a Liverpool player before he returns to Italy to join Sampdoria for £650,000.

Like Keegan, “Souey” was seduced by a new challenge and a rise in his salary, while for the Anfield faithful it was another huge loss to come to terms with. As one supporter put it, Souness was “a bear of a player with the delicacy of a violinist” – the throbbing, masterful heart of a team which ended the 1983-84 season, Joe Fagan’s first as manager, with three trophies – the league, the Milk Cup and that fourth European title. Liverpool were at the peak of their powers and now a man central to all of it, literally as well as figuratively, was leaving.

What happened next? Highly rated Danish midfielder Jan Molby arrived from Ajax, but aged 21 he was not ready to replace Souness. Instead, Fagan used Mark Lawrenson and then Kevin MacDonald to fill the midfield void. But neither came close to matching Souness’s impact and Liverpool struggled, finishing second to Everton in the league. They did reach another European Cup final, but pre-Hillsborough this would be the darkest moment in the club’s history. The 1985 Heysel disaster led to the death of 39 spectators. In Genoa, Souness settled quickly and helped Sampdoria to a first Coppa Italia title in his first season at the club.

Ian Rush (Juventus, 1987)

Ian Rush broke the 40-goal barrier for Liverpool in his final season before joining Juventus. He returned to Anfield a season later. Photograph: ANL/Rex Shutterstock; Getty Images

Everton supporters are quick to point out how the ban on English teams competing in Europe as a result of Heysel affected their club, but across Stanley Park the pain of inaction on the continent was also felt, albeit in self-inflicting circumstances. Liverpool’s team of the mid- to-late-’80s were also denied the chance to prove they could win the European Cup, and as a direct consequence their most potent striker of the era felt he had little choice but to move on.

Ian Rush, like Keegan before him, announced a season in advance that he was departing Anfield for a challenge abroad. He had just helped Liverpool to their first double, scoring twice in the all-Merseyside FA Cup final, and alongside Dalglish formed the most lethal strike partnership in the country. But with Liverpool banned from Europe and his native Wales consistently failing to qualify for major international tournaments, Rush was ready to walk away. “I wanted to see how it was to play against the top foreign players in the world” he later said of his £3.2m move to Juventus.

Having heard of their No9’s intentions, Liverpool fans launched a “Rushie Must Stay” campaign in the summer of 1986, but the man with the bushy ’tasche was not for turning. He at least departed on a high – breaching the 40-goal barrier for the second time in his career during the 1986-87 season.

What happened next? Aware Rush was going at the end of the season, Dalglish signed John Aldridge from Oxford United in January 1987. The pair looked similar but performed in different styles, with Aldridge proving the perfect poacher in Liverpool’s most attractive side – the class of ’87-88, which won the First Division title at a canter. Rush watched on from Turin and couldn’t wait to come back. To this day he disputes saying the infamous quote about Italy being “like a foreign country,” but after just a few months there he was feeling homesick and secured a shock return to Liverpool after only one season away.

Steve McManaman (Real Madrid, 1999)

Steve McManaman left Liverpool for Real Madrid on a Bosman transfer and won the Champions League in his first season with the Spanish club. Photograph: Allsport/Getty Images

Liverpool didn’t sell Steve McManaman and that ultimately was the salt in his wounding departure from the club. A youth product who had become Anfield’s most consistently creative force during the 1990s, the winger left for nothing in the summer of 1999 on a Bosman transfer. It was a messy affair with the ’98-99 season dominated by talk of whether or not McManaman was going to sign a new contract at Liverpool, and with each passing week that he didn’t it looked increasingly the case that he was running down his deal before a move away. Confirmation of that manoeuvre came in January ’99 when the then 26-year-old announced he would be swapping Merseyside for Madrid in six months’ time.

To some extent the time was right for player and club to separate. Liverpool were in decline and under Gérard Houllier were about to embark on a huge overhaul of personnel. McManaman almost certainly would have been kept on but he’d gone a little stale and perhaps needed a new challenge. Few could also blame him for being enticed by the prospect of playing at the Bernabéu every other week, particularly given Liverpool’s struggles and the fact he was strangely unloved by the Anfield fans.

Nevertheless, his exit represented the loss of one of the few top-level talents in Liverpool’s team at that time and the fact the club missed out on a sizeable fee for the player – in the region of £12-16m – only added to the sense that this once mighty institution was in a tailspin.

What happened next? Houllier did indeed ring the changes at Anfield, selling the likes of David James and Paul Ince and bringing in a host of largely low-profile foreign players. They proved a success, however, as Liverpool finished fourth and just missed out on qualification for the Champions League. Speaking of the Champions League, McManaman won it in his first season with Real, scoring in a 3-0 final victory over Valencia.

Michael Owen (Real Madrid, 2004)

Michael Owen came through the youth ranks at Anfield and left to join Real Madrid for £8m at a time when Liverpool were off the pace at home and in Europe. Photograph: Allsport/Getty Images; Getty Images

Two decades after Souness’s departure, Liverpool were facing the very real prospect of losing another midfield colossus. Steven Gerrard was with the England squad at Euro 2004 and giving serious consideration to joining Chelsea. Ultimately he decided to stay at his boyhood club after speaking with his family and Liverpool’s recently appointed manager Rafael Benítez after he had travelled to Portugal to talk face-to-face with the player. However, someone else who was at that meeting had not been persuaded by the Spaniard’s vision.

Michael Owen was perhaps always destined to leave Liverpool sooner rather than later. Despite coming through the club’s youth ranks there was always the sense that he would instantly up and leave if he felt, to use that well-worn cliché, ‘the club did not match his ambitions’. By 2004 Liverpool were off the pace at home and in Europe so it was not a huge surprise when Owen did the opposite to Gerrard and listened to his head over his heart and pushed for a move to Real.

Yet again Liverpool had lost a top talent at a time of uncertainty at the club, and while the supporters could understand a player being enticed by Real there was frustration among them that Owen had not given Benítez at least one season to prove he could be a success on Merseyside. The £8m fee Liverpool received for the player also seemed rather low. They did get winger Antonio Núñez as part of the deal but he proved to be a makeweight on the pitch too.

What happened next? Istanbul. Less than 12 months after Owen turned his back on Liverpool, the club experienced its most memorable night. A fifth European Cup achieved against the odds. Owen could only watch on and wonder what might have been having won nothing during his debut season at Real. And despite doing well – he scored 19 goals in 43 games for the Spanish club – the striker was soon told he had no future at the Bernabéu.

Xabi Alonso (Real Madrid, 2009)

Xabi Alonso left Liverpool for Real Madrid for £30m after his relationship with Rafa Benítez, the then manager, had broken down. Photograph: PA Archive; Getty Images

Hindsight, as they say, is a wonderful thing, and it’s easy to look back now and scoff at Liverpool’s willingness to sell Xabi Alonso in the summer of 2008 so they could sign Gareth Barry. But back then there was method in the madness. Alonso had just endured a difficult campaign while Barry’s reputation was soaring. He also fitted Benítez’s desire to sign a left-footed British midfielder who could operate in other positions. But after protracted talks between Liverpool and Aston Villa, Barry joined Manchester City instead while Alonso, who had been heavily linked with Arsenal, remained at Anfield. It was what happened next that made Benítez look the fool.

Alonso was exceptional during the 2008/09 season, Liverpool’s most consistent performer as they came within four points of clinching the Premier League title. He was a metronome in red, dictating the team’s play from a central midfield position and scoring the odd crucial goal, most notably in a 1-0 win at Chelsea in October ’08. In the space of 12 months Alonso had gone from replaceable to utterly key to Liverpool’s fortunes. What a blow for the club, then, when he handed in a transfer request shortly after the campaign.

Alonso’s relationship with Benítez had broken down and all that was left for Liverpool’s manager was to get the highest possible fee for his compatriot. Real eventually paid £30m for the midfielder and for the third time in 10 years had taken a jewel from Anfield’s crown.

What happened next? Liverpool signed Alberto Aquilani from Roma. He cost £20m, was injured when he arrived and proved to be a completely different player to Alonso. In other words, the Italian was a disastrous purchase. The team also suffered a disastrous campaign, finishing seventh in the Premier League and exiting the Champions League at the group stages. Off the pitch, the Hicks and Gillett-inspired civil war also cost Benítez his job. Alonso, meanwhile, fitted in well at Real and would go on to win La Liga, Copa del Rey and Champions League titles with the Spanish club.

Javier Mascherano (Barcelona, 2010)

Javier Mascherano had been a target for Barcelona in 2009 but Liverpool held on to him for one final full season before he made the move. Photograph: Getty Images

If Alonso was the conductor of Liverpool’s 08-09 band then Javier Mascherano was its heavy metal drummer. A snarling, combative presence, the Argentina international arrived at Anfield on loan in 2007 following his strange failure at West Ham before sealing an £18m transfer 12 months later. Mascherano quickly became a fans’ favourite – part of the Kop’s “best midfield in the world” – but following Alonso’s departure and Liverpool’s struggles during the 09-10 season, it felt inevitable that he would be the next big-name departure from the club.

Barcelona tried to sign the player in the summer of 2009 but failed to do so. They returned 12 months later and this time Mascherano made it clear he wanted to join the Spanish club, citing his wife’s inability to settle in England as his primary motivation. Liverpool resisted but with boardroom unrest growing and Roy Hodgson now in the manager’s dugout, they were hardly at their strongest. In fact, the club was in turmoil and no one could blame a player of Mascherano’s calibre for wanting to jump from a sinking ship.

The shame lay in how the 26-year-old engineered his “dream” move, refusing as he did to take part in Liverpool’s league match at Manchester City and Europa League visit to Trabzonspor in August 2010. He joined Barcelona for £17.25m at the end of the month.

What happened next? Off the pitch Liverpool flirted with administration and on it they did the same with relegation. This was a full-blown crisis, the like of which had never been seen at the club, and it took a victory in the high court and the return of Dalglish as manager in January 2011 to lift the dark clouds over Anfield. All of which was of little concern to Mascherano as he won La Liga and the Champions League in his first season at Camp Nou.

Fernando Torres (Chelsea, 2011)

The departure of the prolific Fernando Torres came as a serious blow to Liverpool fans but the striker struggled at Chelsea. Photograph: Getty Images

Of all the big-name departures Liverpool supporters have had to cope with in the past 30 years it’s arguable none stung more than the one that took place in January 2011. The club was finding its feet again following the horror months of Hicks, Gillett and Hodgson and what was needed was a period of calm under the guidance of new owners, Fenway Sports Group, and a legendary figure of the past. But instead came an almighty punch in the gut when Fernando Torres announced he wanted to leave. Worst of all, he had his heart set on a move to Chelsea.

Torres was struggling, with injuries curtailing the full-on brilliance that he had displayed during his first two seasons at Liverpool. But the Spaniard remained a stellar talent and under Dalglish had scored three goals in five appearances while generally appearing to be on his way back to form. Surely he’d give ‘the King’ the chance to oversee a full rehabilitation? No. Torres wanted out and made that clear by handing in a transfer request just days before the close of the window.

The 26-year-old moved to Chelsea for a record £50m fee on deadline day and claimed he had achieved his target of playing for “one of the top clubs in the world”. El Niño’s transformation from Anfield hero to villain was complete.

What happened next? As was the case in 1977, Liverpool replaced a great striker with an even greater one – and no, not Andy Carroll. Luis Suárez had been signed from Ajax to play alongside Torres but instead he became the focal point of the club’s attack and took to the role with relish. And as the Uruguayan dazzled, Torres increasingly struggled at Stamford Bridge. He may have played a part in Champions League and Europa League triumphs during his time there but overall the £50m man flopped.

Luis Suárez (Barcelona, 2014)

Luis Suárez inspired Liverpool to the brink of their first title in 24 years and was sorely missed after he left for Barcelona, where he won trophies including the European Cup last season. Photograph: Getty Images

If it’s possible to have a whirlwind romance in football than Suárez was Liverpool’s. He arrived in January 2011, left in July 2014, and in between made the club’s supporters feel a full range of emotions – from love, joy, and elation to anger, disappointment and disgust.

It was perhaps inevitable the forward would spend only a brief time on Merseyside and most clubs would have cashed in after the racism controversy … or after he bit an opposition player … or after he claimed the manager was a liar and demanded a move to Arsenal. But FSG and Brendan Rodgers knew they had a star on their hands and forced Suárez to stay put. In return he scored 31 goals during the 2013-14 season, many of them jaw-dropping, and inspired Liverpool to the brink of their first title in 24 years.

It was only a matter of time before Suárez again agitated for a move and once Barcelona came calling there would be no stopping this most unstoppable of players. Liverpool were also powerless to stand in the 27-year-old’s way once the £75m release clause in his contract had been met. Some senior figures at the club were said to be glad to see the back of the player after he had been hit with another ban for taking a bite out of Giorgio Chiellini at the World Cup, but for the majority of Liverpool fans his departure was a devastating setback.

What happened next? Rickie Lambert and Mario Balotelli were signed during a hefty summer outlay with neither coming close last season to filling the void left by Suárez’s departure. Between them the strikers scored three league goals in 41 appearances, and with Daniel Sturridge injured for the majority of the campaign Rodgers’ side struggled at home and in Europe. Suárez, on the other hand, won the lot during his debut season with Barcelona.