It was one of those passes that only Trent Alexander-Arnold could play. Liverpool had struggled to break down Tottenham in December 2024, Spurs holding strong for 23 minutes despite waves of pressure. And then, Alexander-Arnold delivered the killer ball. He drifted in from the right wing, created the ideal angle, and whipped a cross in between two centre-backs, right onto Luis Diaz’s head.

After finding the net, Diaz careened away in celebration before inviting Alexander-Arnold to join in with him. One of the lasting images of that season, in the end, was Diaz pretending to polish Alexander-Arnold’s boots, so thrilled was the Colombian with his team-mate’s assist.

Unfortunately for many Liverpool fans, that connection is very much a thing of the past. Nearly 18 months later, both players are now practicing their craft elsewhere. Alexander-Arnold is in and out of the XI at Real Madrid while Diaz is enjoying a career-best year at Bayern Munich.

In effect, this is the story of two careers that have taken different trajectories. Alexander-Arnold left Liverpool in his prime, and figured to kick on as soon as he sauntered into the Spanish capital. Diaz, meanwhile, left Liverpool feeling like a bit of a reclamation project – a player who wanted out being given a lifeline, but still with a lot to prove.

Instead, the opposite has been true. Alexander-Arnold, whether it be due to injury woes or tactical teething issues, has struggled. Diaz, handed more space than ever to scamper, create and finish, is making the Bundesliga look remarkably easy. And on Tuesday, they will face off against one another.

Alexander-Arnold comes into Champions League quarter-final not only with doubts remaining over him in Madrid, but also with major uncertainty regarding his place in the England pecking order. And so if he can’t lock down his former Liverpool team-mate over the next eight days, then any hope of him reclaiming a place in Thomas Tuchel’s squad for the World Cup will surely be over.

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Immediate chemistry

Diaz’s arrival on Merseyside in January 2022 brought an extra spark to Liverpool. It was clear that Sadio Mane was likely leave the club at the end of that season, and while Spurs were ready to strike for Diaz after some impressive displays for Porto, Liverpool got in early to ensure their Mane succession plan was secured before the Senegalese even left Anfield.

“It is always exciting when we get a new player in to see how he will fit in, how he plays, how he is in training, what he is about, but he’s fit in straight away,” Alexander-Arnold said of Diaz two weeks after the Reds shelled out just shy of €50 million for the winger.

Diaz’s adaptation to the Premier League, admittedly, took a bit of time, but his connection with Alexander-Arnold was immediate. The right-back assisted him on just three occasions during the three seasons they shared on Merseyside, yet the creative understanding was clear from early on. A common sight as Jurgen Klopp’s Liverpool tactically evolved would be Alexander-Arnold drifting inside and playing a raking pass to the left flank, which Diaz would eagerly ran on to.

And, of course, the two shared immense success on the pitch. During three-and-a-half seasons together, they won two League Cups, an FA Cup and the Premier League.