Liverpool were drawn in the same Champions League group as AC Milan for this season’s edition of the competition, setting up two mouth-watering clashes between two European heavyweights.
Despite the sides’ respective histories in continental competition, they have only ever met twice before in official games.
And both of those were huge occasions – that incredible comeback in Istanbul in 2005, and the Champions League final rematch two years later which saw the Italians run out as winners.
The stakes won’t quite be so high for their next two meetings in this year’s group stage, but they represent interesting fixtures considering the few meetings between the clubs before.
While Liverpool and Milan haven’t often shared a football pitch, the same is not so true for a number of players who have pulled on the famous strips of both clubs in their careers – with varying degrees of success.
Here are some of the more recognisable:
Mario BalotelliEmbed from Getty Images
He’d always been known as a bit of a footballing bad boy long before he moved to Merseyside, yet there was still some hope Balotelli would be able to make an impact after being brought in as a replacement for Luis Suárez.
But it quickly became apparent the Italian would not be able to provide anything like the attacking threat and consistent goals the Uruguayan did during his time at Anfield.
Instead, just one league goal in 16 league appearances for the Reds in 2014/15 was an awful return for a £16m striker, who had joined directly from Milan after a successful season in Serie A.
He had managed 14 goals in 30 league outings for the Rossoneri, but did not get anywhere close to this sort of return either on Merseyside or when loaned back to Milan for the 2015/16 campaign.
It was clear Balotelli’s career was stuttering and, with two years left to go on his Liverpool contract, he was allowed to leave in the summer of 2016 on a free transfer to Nice.
A costly failure for the Liverpool transfer team.
Fabio BoriniEmbed from Getty Images
Another Italian who failed to ever really get going at Anfield, Borini was cruelly denied a chance to ever show what he could do due to injuries in his first season.
When he was signed from Roma following Euro 2012, there were hopes that Liverpool would be able to get the best out of a Chelsea youth product who had impressed in a loan spell with Swansea City before 10 goals in a 14-game run with Roma.
There was brief belief that might be the case after he netted in his debut match, a Europa League qualifier against Belarusian side FC Gomel, but he then broke a bone in his foot which ensured he would not see first-team action again until 2013.
Another injury in February, and the arrival of Daniel Sturridge who hit the ground running following his move from Chelsea, meant Borini’s first season was a complete write-off except for that strike against Gomel and netting one of the six against Newcastle United in April.
A successful loan at Sunderland the following campaign saw a permanent move materialise but, after the Black Cats were relegated, he moved on loan to Milan.
His performances back in his homeland were good enough to convince Milan to bring him in permanently, though he later found appearances for the Rossoneri hard to come by.
Borini was later moved on to Hellas Verona, before being released and finding himself without a club for six months before joining current club Fatih Karagümrük in the Turkish Süper Lig.
Pepe ReinaEmbed from Getty Images
Pepe Reina was a very experienced 22-year-old when he arrived at Liverpool in 2005, having made almost 200 appearances for Barcelona and Villarreal and establishing himself as a dependable stopper and penalty kick specialist.
Replacing Jerzy Dudek, whose heroics just weeks earlier had helped the Reds pull of THAT comeback against Milan in Istanbul, was going to be no easy task for the Spaniard.
But it didn’t take him long, as Rafa Benítez was clearly set on making his compatriot the preferred No.1 for his time at Anfield.
He quickly won the fans over, no doubt helped by his penalty-saving success in the FA Cup final at the end of his debut season, and for the first few years looked an entirely solid and dependable option between the sticks.
Reina had two ropey years between 2010 and 2012, looking like he had lost confidence and had struggled with his weight a little too. But the 2012/13 campaign saw the Spaniard return to his best form and it looked like he would continue into his 30s as Liverpool’s undisputed No.1.
But suddenly, Simon Mignolet was signed from Sunderland and Reina, it was announced, would be heading to Napoli on loan, leaving his appearance total for Liverpool just six shy of 400.
Since leaving permanently for Bayern Munich in 2014, with the exception of a later spell back in Naples, Reina has generally been a second-choice option – including at Milan where he played second fiddle to Gianluigi Donnarumma.
But a loan to Aston Villa gave him a new lease of life, impressing enough not only to join Lazio but to convince first Simone Inzaghi and now Maurizio Sarri to make him their preferred option ahead of Thomas Strakosha.
SusoEmbed from Getty Images
Moving from his boyhood club Cádiz to Liverpool, Rafa Benítez had made it one of his final acts at the Liverpool helm to convince the talented young Spaniard to reject the advances of Real Madrid and Barcelona to instead move to England.
Suso was quickly recognised as a future star by coaches on Merseyside and fast-tracked into the reserves side, but neither Roy Hodgson nor Kenny Dalglish were convinced enough just yet to bring him into the first-team picture.
That changed when Brendan Rodgers took over, who clearly liked what he saw and wasted little time in giving Suso some opportunities in the senior side.
A total of 20 appearances out of 54 games in 2012/13 was a promising return for a teenager, but the majority of those had come in the first half of the campaign before the arrival and strong form of Philippe Coutinho had limited his opportunities.
A loan to Almería for 2013/14 beckoned, before Suso was surprisingly allowed to join AC Milan in a free transfer in January 2015.
He struggled initially with the Italian giants, but a loan to Genoa helped get the ball rolling and, from the beginning of the 2016/17 campaign, he was a regular at the San Siro.
No-one in Serie A managed more assists than the Spaniard in that breakout season, and he continued his fine form for two more campaigns, which even led to several caps for the Spanish national side.
The emergence of compatriot Samu Castillejo limited his chances, so he moved to Sevilla on loan before making the move permanent last summer – after making Liverpool fans very happy by netting in a 2-1 victory to knock Manchester United out of European competition.
Now 27, he remains with Sevilla. He will be pleased with where his career is after stalling at Liverpool, but going on to thrive after trading in Merseyside for Milan.
Fernando TorresEmbed from Getty Images
Fernando Torres was brought to Liverpool from Atlético Madrid as a marquee signing, unveiled on the July 4 Independence Day holiday by the club’s American owners.
He was eased in somewhat by Benítez, to the frustration of some fans who had been impressed by what they had seen in his early appearances and wanted to see more of their new main man up front.
It wouldn’t be long until they got their wish, and Torres went on to average well over a goal every other game during his three-and-a-half years on Merseyside.
The circumstances surrounding the Spaniard’s departure were acrimonious to say the least, and there will understandably be many who cannot bring themselves to forgive him for leaving Liverpool to join Chelsea.
But the simple, painful truth is the Reds were going nowhere at the time, while the Londoners were challenging for trophies every season.
After falling out of favour at Stamford Bridge in 2014 he was loaned to Milan, where he made 10 appearances and scored one goal in a 2-2 draw against Empoli before the Italians confirmed they had made his move permanent.
It seems they never planned to involve him in the first team, though, as just two days later he was loaned back to Atlético before making his move back to his boyhood club permanent.
He stayed for two seasons before ending his career with a spell at Sagan Tosu, joining fellow Spanish star Andrés Iniesta in the Japanese league.
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